Substituted herbicide tetrazolinonecarboxylic acid amides

ABSTRACT

Tetrazolinonecarboxamides of formula I                    
     wherein 
     Het is oxetan-3-yl, thietan-3-yl, tetrahydrofuran-3-yl, furan-3-yl, tetrahydrothiophen-3-yl, thiophen-3-yl, tetrahydro-2H-pyran-3-yl, tetrahydro-2H-thiopyran-3-yl, tetrahydro-2H-pyran-4-yl or tetrahydro-2H-thiopyran-4-yl, in each case with or without substitution; 
     R 1  is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl, or 3- to 7-membered heterocyclyl; 
     R 2  is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, or is optionally substituted cycloalkyl, cycloalkylalkyl, phenyl, phenylalkyl, 3- to 7-membered heterocyclyl, or 3- to 7-membered heterocyclylalkyl, 
     their preparation and herbicidal compositions comprising them.

This application is a 371 of PCT/EP98/04480 filed Jul. 20, 1998.

The present invention relates to novel substituted tetrazolinonecarboxamides of the formula I

where the variables have the following meaning:

Het is oxetan-3-yl, thietan-3-yl, tetrahydrofuran-3-yl, furan-3-yl, tetrahydrothiophen-3-yl, thiophen-3-yl, tetrahydro-2H-pyran-3-yl, tetrahydro-2H-thiopyran-3-yl, tetrahydro-2H-pyran-4-yl or tetrahydro-2H-thiopyran-4-yl,

where the abovementioned heterocycles may carry one or two substituents selected from a group consisting of halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl;

R¹ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C-C₄-alkyl, C₁-C₄-haloalkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁C₄-haloalkylsulfonyl-C₁-C₄-alkyl, C₂-C₆-alkenyl, cyano-C₃-C₆-alkenyl, C₂-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₅-C₈-cycloalkenyl, C₅-C₈-cycloalkenyl-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, 3- to 7-membered heterocyclyl, which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C₁-C₄-alkyl, which may contain a carbonyl or thiocarbonyl ring member;

where the cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings may in each case be unsubstituted or carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkylcarbonyloxy and C₁-C₄-haloalkylcarbonyloxy; heterocyclyl- C₁-C₄-alkyl which may contain a carbonyl or thiocarbonyl ring member,

the cycloalkyl rings, phenyl rings or heterocyclyl rings being with or without substitution, and herbicidal compositions comprising the tetrazolinonecarboxamides I.

R² is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, 3- to 7-membered heterocyclyl, which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C₁-C₄-alkyl, which may contain a carbonyl or thiocarbonyl ring member,

where the cycloalkyl rings, phenyl rings or heterocyclyl rings are in each case unsubstituted or carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkylcarbonyloxy and C₁-C₄-haloalkylcarbonyloxy.

Furthermore, the invention relates to processes for preparing substituted tetrazolinonecarboxamides of the formula I, to their use as herbicides, to herbicidal compositions comprising the substituted tetrazolinonecarboxamides of the formula I as active substances, to processes for preparing these herbicidal compositions and to methods for controlling undesirable vegetation.

Herbicidally active tetrazolinonecarboxamides are described, for example, in EP-A-146 279. Tetrazolinonecarboxamides which are cycloalkyl- substituted at the amide nitrogen and have herbicidal activity are disclosed, for example, in EP-A-692 482, EP-A-672 663, EP-A-612 735, EP-A-732 326, EP-A-202 929, EP-A-712 850, EP-A-711 761, EP-A-708 097, EP-A-728 750, EP-A-695 748, EP-A-733 625, EP-A-733 624.

However, the herbicidal properties of the known herbicides with respect to harmful plants are not entirely satisfactory.

It is an object of the present invention to provide novel herbicidally active compounds which allow better control of undesirable plants.

We have found that this object is achieved by the present substituted tetrazolinonecarboxamides of the formula I and their herbicidal activity.

Furthermore, we have found herbicidal compositions comprising the compounds I and having very good herbicidal activity. Furthermore, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they exist in the form of enantiomer or diastereomer mixtures. This invention provides both the pure enantiomers or diastereomers and mixtures thereof.

The organic moieties mentioned for the substituents Het, R¹, R² or as radicals on cycloalkyl, phenyl or heterocyclyl rings are collective terms for the individual listings of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, cyanoalkyl, phenylalkyl, heterocyclylalkyl, alkylcarbonyl, haloalkylcarbonyl, alkylcarbonyloxy, haloalkylcarbonyloxy, alkoxycarbonyl, alkenyl, haloalkenyl, cyanoalkenyl and alkynyl groups can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms.

The term halogen represents in each case fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine.

Examples of other meanings are:

C₁-C₄-alkyl: CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, 1-methylpropyl, 2-methylpropyl or C(CH₃)₃; in particular CH₃ or C₂H₅;

C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above, or, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; in particular CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, C(CH₃)₃, n-pentyl or n-hexyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example CH₂Cl, CH(Cl)₂, C(Cl)₃, CH₂F, CHF₂, CF₃, CHFCl, CF(Cl)₂, CF₂Cl, CF₂Br, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1,2-dichloroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl; in particular chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 1,2-dichloroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl;

C₁-C₆-haloalkyl: C₁-C₆-alkyl as mentioned above, which is partially or fully substituted by fluorine, chlorine and/or bromine, i.e. for example one of the abovementioned C₁-C₄-haloalkyl radicals, or 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, 5,5,5-trichloropentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, 6,6,6-trichlorohexyl or dodecafluorohexyl; in particular fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

C₃-C₈-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl; in particular cyclopentyl or cyclohexyl;

C₅-C₈-cycloalkenyl: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1-enyl, cyclohept-2-enyl, cyclohept-3-enyl, cyclohept-4-enyl, cyclooct-1-enyl, cyclooct-2-enyl, cyclooct-3-enyl or cyclooct-4-enyl; in particular cyclopent-1-enyl or cyclohex-1-enyl;

C₁-C₄-alkoxy and the alkoxy radicals of alkoxycarbonylalkoxy: OCH₃, OC₂H₅, n-propoxy, OCH(CH₃)₂, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or OC(CH₃)₃; in particular OCH₃, OC₂H₅, OCH(CH₃)₂ or OC(CH₃)₃;

C₁-C₄-haloalkoxy: C₁-C₄-alkoxy as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example OCH₂Cl, OCH(Cl)₂, OC(Cl)₃, OCH₂F, OCHF₂, OCF₃, OCHFCl, OCF(Cl)₂, OCF₂Cl, OCF₂Br, 1-fluoroethoxy, 2-fluoroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 1,2-dichloroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy; in particular chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 1,2-dichloroethoxy, 2,2,2-trifluoroethoxy or pentafluoroethoxy;

C₁-C₄-alkylthio: SCH₃, SC₂H₅, n-propylthio, SCH(CH₃)₂, n-butylthio, 1-methylpropylthio, 2-methylpropylthio or SC(CH₃)₃; in particular SCH₃ or SC₂H₅;

C₁-C₄-haloalkylthio: C₁-C₄-alkylthio as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example SCH₂Cl, SCH(Cl)₂, SC(Cl)₃, SCH₂F, SCHF₂, SCF₃, SCHFCl, SCF(Cl)₂, SCF₂Cl, SCF₂Br, 1-fluoroethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 1,2-dichloroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutoxy; in particular chloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 1,2-dichloroethylthio, 2,2,2-trifluoroethylthio or pentafluoroethylthio;

C₁-C₄-alkylsulfonyl: SO₂CH₃, SO₂C₂H₅, n-propylsulfonyl, SO₂CH(CH₃)₂, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or SO₂C(CH₃)₃; in particular SO₂CH₃ or SO₂C₂H₅;

C₁-C₄-haloalkylsulfonyl: a C₁-C₄-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example chloromethylsulfonyl, dichloromethylsulfonyl, trichloromethylsulfonyl, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 1,2-dichloroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl; in particular chloromethylsulfonyl, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 1,2-dichloroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl or pentafluoroethylsulfonyl;

cyano-C₁-C₄-alkyl: for example CH₂CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2-yl, 4-cyanobut-2-yl, 1-(CH₂CN)eth-1-yl, 1-(CH₂CN)-1-(CH₃)eth-1-yl or 1-(CH₂CN)prop-1-yl; in particular CH₂CN or 2-cyanoethyl;

phenyl-C₁-C₄-alkyl: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1-(phenylmethyl)eth-1-yl, 1-(phenylmethyl)-1-(methyl)eth-1-yl or 1-(phenylmethyl)prop-1-yl; in particular benzyl or 2-phenylethyl;

C₃-C₈-cycloalkyl-C₁-C₄-alkyl: cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 1-cyclopropylprop-1-yl, 2-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl, 1-cyclopropylbut-1-yl, 2-cyclopropylbut-1-yl, 3-cyclopropyl-but-1-yl, 4-cyclopropylbut-1-yl, 1-cyclopropylbut-2-yl, 2-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl, 3-cyclopropyl-but-2-yl, 4-cyclopropylbut-2-yl, 1-(cyclopropylmethyl)-eth-1-yl, 1-(cyclopropylmethyl)-1-(CH₃)-eth-1-yl, 1-(cyclopropylmethyl)prop-1-yl, cyclobutylmethyl, 1-cyclobutylethyl, 2-cyclobutylethyl, 1-cyclobutylprop-1-yl, 2-cyclobutylprop-1-yl, 3-cyclobutylprop-1-yl, 1-cyclobutylbut-1-yl, 2-cyclobutylbut-1-yl, 3-cyclobutylbut-1-yl, 4-cyclobutylbut-1-yl, 1-cyclobutylbut-2-yl, 2-cyclobutylbut-2-yl, 3-cyclobutylbut-2-yl, 3-cyclobutylbut-2-yl, 4-cyclobutylbut-2-yl, 1-(cyclobutylmethyl)eth-1-yl, 1-(cyclobutylmethyl)-1-(methyl)eth-1-yl, 1-(cyclobutylmethyl)prop-1-yl, cyclopentylmethyl, 1-cyclopentylethyl, 2-cyclopentylethyl, 1-cyclopentylprop-1-yl, 2-cyclopentylprop-1-yl, 3-cyclopentylprop-1-yl, 1-cyclopentylbut-1-yl, 2-cyclopentylbut-1-yl, 3-cyclopentylbut-1-yl, 4-cyclopentylbut-1-yl, 1-cyclopentylbut-2-yl, 2-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl, 4-cyclopentylbut-2-yl, 1-(cyclopentylmethyl)eth-1-yl, 1-(cyclopentylmethyl)-1-(methyl)eth-1-yl, 1-(cyclopentylmethyl)prop-1-yl, cyclohexylmethyl, 1-cyclohexylethyl, 2-cyclohexylethyl, 1-cyclohexylprop-1-yl, 2-cyclohexylprop-1-yl, 3-cyclohexylprop-1-yl, 1-cyclohexylbut-1-yl, 2-cyclohexylbut-1-yl, 3-cyclohexylbut-1-yl, 4-cyclohexylbut-1-yl, 1-cyclohexylbut-2-yl, 2-cyclohexylbut-2-yl, 3-cyclohexylbut-2-yl, 3-cyclohexylbut-2-yl, 4-cyclohexylbut-2-yl, 1-(cyclohexylmethyl)eth-1-yl, 1-(cyclohexylmethyl)-1-(methyl)eth-1-yl, 1-(cyclohexylmethyl)prop-1-yl, cycloheptylmethyl, 1-cycloheptylethyl, 2-cycloheptylethyl, 1-cycloheptylprop-1-yl, 2-cycloheptylprop-1-yl, 3-cycloheptylprop-1-yl, 1-cycloheptylbut-1-yl, 2-cycloheptylbut-1-yl, 3-cycloheptylbut-1-yl, 4-cycloheptylbut-1-yl, 1-cycloheptylbut-2-yl, 2-cycloheptylbut-2-yl, 3-cycloheptylbut-2-yl, 3-cycloheptylbut-2-yl, 4-cycloheptylbut-2-yl, 1-(cycloheptylmethyl)eth-1-yl, 1-(cycloheptylmethyl)-1-(methyl)eth-1-yl, 1-(cycloheptylmethyl)prop-1-yl, cyclooctylmethyl, 1-cyclooctylethyl, 2-cyclooctylethyl, 1-cyclooctylprop-1-yl, 2-cyclooctylprop-1-yl, 3-cyclooctylprop-1-yl, 1-cyclooctylbut-1-yl, 2-cyclooctylbut-1-yl, 3-cyclooctylbut-1-yl, 4-cyclooctylbut-1-yl, 1-cyclooctylbut-2-yl, 2-cyclooctylbut-2-yl, 3-cyclooctylbut-2-yl, 3-cyclooctylbut-2-yl, 4-cyclooctylbut-2-yl, 1-(cyclooctylmethyl)eth-1-yl, 1-(cyclooctylmethyl)-1-(methyl)-eth-1-yl or 1-(cyclooctylmethyl)prop-1-yl; in particular C₃₋C₆ ₋cycloalkylmethyl;

C₅-C₈-cycloalkenyl-C₁-C₄-alkyl: (cyclopent-1-enyl)methyl, (cyclopent-2-enyl)methyl, (cyclopent-3-enyl)methyl, 1-(cyclopent-1-enyl)ethyl, 1-(cyclopent-2-enyl)ethyl, 1-(cyclopent-3-enyl)ethyl, 2-(cyclopent-1-enyl)ethyl, 2-(cyclopent-2-enyl)ethyl, 2-(cyclopent-3-enyl)ethyl, 1-(cyclopent-1-enyl)prop-1-yl, 1-(cyclopent-2-enyl)prop-1-yl, 1-(cyclopent-3-enyl)prop-1-yl, 2-(cyclopent-1-enyl)prop-1-yl, 2-(cyclopent-2-enyl)prop-1-yl, 2-(cyclopent-3-enyl)prop-1-yl, 3-(cyclopent-1-enyl)prop-1-yl, 3-(cyclopent-2-enyl)prop-1-yl, 3-(cyclopent-3-enyl)prop-1-yl, 1-(cyclopent-1-enyl)but-1-yl, 1-(cyclopent-2-enyl)but-1-yl, 1-(cyclopent-3-enyl)but-1-yl, 2-(cyclopent-1-enyl)but-1-yl, 2-(cyclopent-2-enyl)but-1-yl, 2-(cyclopent-3-enyl)but-1-yl, 3-(cyclopent-1-enyl)but-1-yl, 3-(cyclopent-2-enyl)but-1-yl, 3-(cyclopent-3-enyl)but-1-yl, 4-(cyclopent-1-enyl)but-1 -yl, 4-(cyclopent-2-enyl)but-1-yl, 4-(cyclopent-3-enyl)but-1-yl, 1-(cyclopent-1-enyl)but-2-yl, 1-(cyclopent-2-enyl)but-2-yl, 1-(cyclopent-3-enyl)but-2-yl, 2-(cyclopent-1-enyl)but-2-yl, 2-(cyclopent-2-enyl)but-2-yl, 2-(cyclopent-3-enyl)but-2-yl, 3-(cyclopent-1-enyl)but-2-yl, 3-(cyclopent-2-enyl)but-2-yl, 3-(cyclopent-3-enyl)but-2-yl, 4-(cyclopent-1-enyl)but-2-yl, 4-(cyclopent-2-enyl)but-2-yl, 4-(cyclopent-3-enyl)but-2-yl, 1-((cyclopent-1-enyl)-methyl)eth-1-yl, 1-((cyclopent-2-enyl)methyl)eth-1-yl, 1-((cyclopent-3-enyl)-methyl)eth-1-yl, 1-((cyclopent-1-enyl)methyl)-1-(methyl)eth-1-yl, 1-((cyclopent-2-enyl)-methyl)-1-(methyl)eth-1-yl, 1-((cyclopent-3-enyl)-methyl)-1-(methyl)eth-1-yl, 1-((cyclopent-1-enyl)-methyl)-prop-1-yl, 1-((cyclopent-2-enyl)methyl)prop-1-yl, 1-((cyclopent-3-enyl)methyl)prop-1-yl, (cyclohex-1-enyl)methyl, (cyclohex-2-enyl)methyl, (cyclohex-3-enyl)methyl, 1-(cyclohex-1-enyl)ethyl, 1-(cyclohex-2-enyl)ethyl, 1-(cyclohex-3-enyl)ethyl, 2-(cyclohex-1-enyl)ethyl, 2-(cyclohex-2-enyl)-ethyl, 2-(cyclohex-3-enyl)ethyl, 1-(cyclohex-1-enyl)prop-1-yl, 1-(cyclohex-2-enyl)prop-1-yl, 1-(cyclohex-3-enyl)prop-1-yl, 2-(cyclohex-1-enyl)prop-1-yl, 2-(cyclohex-2-enyl)prop-1-yl, 2-(cyclohex-3-enyl)prop-1-yl, 3-(cyclohex-1-enyl)prop-1-yl, 3-(cyclohex-2-enyl)prop-1-yl, 3-(cyclohex-3-enyl)prop-1-yl, 1-(cyclohex-1-enyl)but-1-yl, 1-(cyclohex-2-enyl)but-1-yl, 1-(cyclohex-3-enyl)but-1-yl, 2-(cyclohex-1-enyl)but-1-yl, 2-(cyclohex-2-enyl)but-1-yl, 2-(cyclohex-3-enyl)but-1-yl, 3-(cyclohex-1-enyl)but-1-yl, 3-(cyclohex-2-enyl)but-1-yl, 3-(cyclohex-3-enyl)but-1-yl, 4-(cyclohex-1-enyl)but-1-yl, 4-(cyclohex-2-enyl)but-1-yl, 4-(cyclohex-3-enyl)but-1-yl, 1-(cyclohex-1-enyl)but-2-yl, 1-(cyclohex-2-enyl)but-2-yl, 1-(cyclohex-3-enyl)but-2-yl, 2-(cyclohex-1-enyl)but-2-yl, 2-(cyclohex-2-enyl)but-2-yl, 2-(cyclohex-3-enyl)but-2-yl, 3-(cyclohex-1-enyl)but-2-yl, 3-(cyclohex-2-enyl)but-2-yl, 3-(cyclohex-3-enyl)but-2-y1, 4-(cyclohex-1-enyl)but-2-yl, 4-(cyclohex-2-enyl)but-2-yl, 4-(cyclohex-3-enyl)but-2-yl 1-((cyclohex-1-enyl)methyl)eth-1-yl, 1-(cyclohex-2-enyl)methyl)eth-1-yl, 1-((cyclohex-3-enyl)methyl)eth-1-yl, 1-((cyclohex-1-enyl)methyl)-1-(methyl)eth-1-yl, 1-((cyclohex-2-enyl)methyl)-1-(methyl)eth-1-yl, 1-((cyclohex-3-enyl)methyl)-1-(methyl)eth-1-yl, 1-((cyclohex-1-enyl)methyl)prop-1-yl, 1-((cyclohex-2-enyl)methyl)prop-1-yl, 1-((cyclohex-3-enyl)methyl)prop-1-yl,(cyclohept-1-enyl)methyl, (cyclohept-2-enyl)methyl, (cyclohept-3-enyl)methyl, (cyclohept-4-enyl)methyl, 1-(cyclohept-1-enyl)ethyl, 1-(cyclohept-2-enyl)ethyl, 1-(cyclohept-3-enyl)ethyl, 1-(cyclohept-4-enyl)ethyl, 2-(cyclohept-1-enyl)ethyl, 2-(cyclohept-2-enyl)ethyl, 2-(cyclohept-3-enyl)ethyl, 2-(cyclohept-4-enyl)ethyl, 1-(cyclohept-1-enyl)prop-1-yl, 1-(cyclohept-2-enyl)prop-1-yl, 1-(cyclohept-3-enyl)prop-1-yl, 1-(cyclohept-4-enyl)prop-1-yl, 2-(cyclohept-1-enyl)prop-1-yl, 2-(cyclohept-2-enyl)prop-1-yl, 2-(cyclohept-3-enyl)prop-1-yl, 2-(cyclohept-4-enyl)prop-1-yl, 3-(cyclohept-1-enyl)prop-1-yl, 3-(cyclohept-2-enyl)prop-1-yl, 3-(cyclohept-3-enyl)prop-1-yl, 3-(cyclohept-4-enyl)prop-1-yl, 1-(cyclohept-1-enyl)but-1-yl, 1-(cyclohept-2-enyl)but-1-yl, 1-(cyclohept-3-enyl)but-1-yl, 1-(cyclohept-4-enyl)but-1-yl, 2-(cyclohept-1-enyl)but-1-yl, 2-(cyclohept-2-enyl)but-1-yl, 2-(cyclohept-3-enyl)but-1-yl, 2-(cyclohept-4-enyl)but-1-yl, 3-(cyclohept-3-enyl)but-1-yl, 3-(cyclohept-2-enyl)but-1-yl, 3-(cyclohept-3-enyl)but-1-yl, 3-(cyclohept-4-enyl)but-1-yl, 4-(cyclohept-1-enyl)but-1-yl, 4-(cyclohept-2-enyl)but-1-yl, 4-(cyclohept-3-enyl)but-1-yl, 4-(cyclohept-4-enyl)but-1-yl, 1-(cyclohept-1-enyl)but-2-yl, 1-(cyclohept-2-enyl)but-2-yl, 1-(cyclohept-3-enyl)but-2-yl, 1-(cyclohept-4-enyl)but-2-yl, 2-(cyclohept-3-enyl)but-2-yl, 2-(cyclohept-2-enyl)but-2-yl, 2-(cyclohept-3-enyl)but-2-yl, 2-(cyclohept-4-enyl)but-2-yl, 3-(cyclohept-1-enyl)but-2-yl, 3-(cyclohept-2-enyl)but-2-yl, 3-(cyclohept-3-enyl)but-2-yl, 3-(cyclohept-4-enyl)but-2-yl, 4-(cyclohept-3-enyl)but-2-yl, 4-3(cyclohept-2-enyl)but-2-yl, 4-(cyclohept-3-enyl)but-2-yl, 4-(cyclohept-4-enyl)but-2-yl, 1-((cyclohept-1-enyl)methyl)eth-1-yl, 1-((cyclohept-2-enyl)methyl)eth-1-yl, 1-((cyclohept-3-enyl)methyl)eth-1-yl, 1-((cyclohept-4-enyl)methyl)eth-1-yl, 1-((cyclohept-1-enyl)methyl)-1-(methyl)eth-1-yl, 1-((cyclohept-2-enyl)methyl)-1-(methyl)eth-1-yl, 1-((cyclohept-3-enyl)methyl)-1-(methyl)eth-1-yl, 1-((cyclohept-4-enyl)methyl)-1-(methyl)eth-1-yl, 1-((cyclohept-1-enyl)methyl)prop-1-yl, 1-((cyclohept-2-enyl)methyl)prop-1-yl, 1-((cyclohept-3-enyl)methyl)prop-1-yl, 1-((cyclohept-4-enyl)methyl)prop-1-yl, (cyclooct-1-enyl)methyl, (cyclooct-2-enyl)methyl, (cyclooct-3-enyl)methyl, (cyclooct-4-enyl)methyl, 1-(cyclooct-1-enyl)ethyl, 1-(cyclooct-2-enyl)ethyl, 1-(cyclooct-3-enyl)ethyl, 1-(cyclooct-4-enyl)ethyl, 2-(cyclooct-1-enyl)ethyl, 2-(cyclooct-2-enyl)ethyl, 2-(cyclo-oct-3-enyl)ethyl, 2-(cyclooct-4-enyl)ethyl, 1-(cyclooct-1-enyl)prop-1-yl, 1-(cyclooct-2-enyl)prop-1-yl, 1-(cyclooct-3-enyl)prop-1-yl, 1-(cyclooct-4-enyl)prop-1-yl, 2-(cyclooct-1-enyl)prop-1-yl, 2-(cyclooct-2-enyl)prop-1-yl, 2-(cyclooct-3-enyl)prop-1-yl, 2-(cyclooct-4-enyl)prop-1-yl, 3-(cyclooct-1-enyl)prop-1-yl, 3-(cyclooct-2-enyl)prop-1-yl, 3-(cyclooct-3-enyl)prop-1-yl, 3-(cyclooct-4-enyl)prop-1-yl, 1-(cyclooct-1-enyl)but-1-yl, 1-(cyclooct-2-enyl)but-1-yl, 1-(cyclooct-3-enyl)but-1-yl, 1-(cyclooct-4-enyl)but-1-yl, 2-(cyclooct-1-enyl)but-1-yl, 2-(cyclooct-2-enyl)but-1-yl, 2-(cyclooct-3-enyl)but-1-yl, 2-(cyclooct-4-enyl)but-1-yl, 3-(cyclooct-1-enyl)but-1-yl, 3-(cyclooct-2-enyl)but-1-yl, 3-(cyclooct-3-enyl)but-1-yl, 3-(cyclooct-4-enyl)but-1-yl, 4-(cyclooct-1-enyl)but-1-yl, 4-(cyclooct-2-enyl)but-1-yl, 4-(cyclooct-3-enyl)but-1-yl, 4-(cyclooct-4-enyl)but-1-yl, 1-(cyclooct-3-enyl)but-2-yl, 1-(cyclooct-2-enyl)but-2-yl, 1-(cyclooct-3-enyl)but-2-yl, 1-(cyclooct-4-enyl)but-2-yl, 2-(cyclooct-1-enyl)but-2-yl, 2-(cyclooct-2-enyl)but-2-yl, 2-(cyclooct-3-enyl)but-2-yl, 2-(cyclooct-4-enyl)but-2-yl, 3-(cyclooct-3-enyl)but-2-yl, 3-(cyclooct-2-enyl)but-2-yl, 3-(cyclooct-3-enyl)but-2-yl, 3-(cyclooct-4-enyl)but-2-yl, 4-(cyclooct-3-enyl)but-2-yl, 4-(cyclooct-2-enyl)but-2-yl, 4-(cyclooct-3-enyl)but-2-yl, 4-(cyclooct-4-enyl)but-2-yl, 1-((cyclooct-1-enyl)methyl)eth-1-yl, 1-((cyclooct-2-enyl)methyl)eth-1-yl, 1-((cyclooct-3-enyl)methyl)eth-1-yl, 1-((cyclooct-4-enyl)methyl)eth-1-yl, 1-((cyclooct-1-enyl)methyl)-1-(CH₃)-eth-1-yl, 1-((cyclooct-2-enyl)methyl)-1-(CH₃)eth-1-yl, 1-((cyclooct-3-enyl)methyl)-1-(CH₃)-eth-1-yl, 1-((cyclooct-4-enyl)methyl)-1-(CH₃)eth-1-yl, 1-((cyclooct-1-enyl)methyl)prop-1-yl, 1-((cyclooct-2-enyl)methyl)prop-1-yl, 1-((cyclooct-3-enyl)methyl)prop-1-yl, 1-((cyclooct-4-enyl)methyl)prop-1-yl; in particular C₅-C₆-cycloalkenylmethyl;

heterocyclyl-C₁-C₄-alkyl: heterocyclylmethyl, 1-(heterocyclyl)ethyl, 2-(heterocyclyl)ethyl, 1-(heterocyclyl)prop-1-yl, 2-(heterocyclyl)prop-1-yl, 3-(heterocyclyl)prop-1-yl, 1-(heterocyclyl)but-1-yl, 2-(heterocyclyl)but-1-yl, 3-(heterocyclyl)but-1-yl, 4-(heterocyclyl)but-1-yl, 1-(heterocyclyl)but-2-yl, 2-(heterocyclyl)but-2-yl, 3-(heterocyclyl)but-2-yl, 3-(heterocyclyl)but-2-yl, 4-(heterocyclyl)but-2-yl, 1-(heterocyclylmethyl)eth-1-yl, 1-(heterocyclylmethyl)-1-(CH₃)-eth-1-yl or 1-(hetero-cyclylmethyl)prop-1-yl; in particular heterocyclylmethyl or 2-(heterocyclyl)ethyl,

C₁-C₄-alkoxy-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted by C₁-C₄-alkoxy as mentioned above, i.e. for example CH₂OCH₃, CH₂OC₂H₅, n-propoxymethyl, (1-methylethoxy)methyl, n-butoxy-methyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(OCH₃)propyl, 2-(OC₂H₅)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(OCH₃)propyl, 3-(OC₂H₅)propyl, 3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(OCH₃)butyl, 2-(OC₂H₅)butyl, 2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(OCH₃)butyl, 3-(OC₂H₅)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(OCH₃)butyl, 4-(OC₂H₅)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl; in particular methoxymethyl or 2-methoxyethyl;

C₁-C₄-haloalkoxy-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted by C₁-C₄-haloalkoxy as mentioned above, i.e. for example 2-(difluoromethoxy)ethyl, 2-(trifluoromethoxy)ethyl or 2-(pentafluoroethoxy)ethyl;

C₁-C₄-alkylthio-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted by C₁-C₄-alkylthio as mentioned above, i.e. for example CH₂SCH₃, CH₂SC₂H₅, n-propylthiomethyl, CH₂SCH(CH₃)₂, n-butylthiomethyl, (1-methylpropylthio)methyl, (2-methylpropylthio)methyl, CH₂SC(CH₃)₃, 2-methylthioethyl, 2-ethylthioethyl, 2-(n-propylthio)ethyl, 2-(1-methylethylthio)ethyl, 2-(n-butylthio)ethyl-2-(-methylpropylthio)ethyl, 2-(2-methylpropylthio)ethyl, 2-(1,1-dimethylethylthio)ethyl, 2-(SCH₃)propyl, 3-(SCH₃)propyl, 2-(SC₂H₅)propyl, 3-(SC₂H₅)propyl, 3-(propylthio)propyl, 3-(butylthio)propyl, 4-(SCH₃)butyl, 4-(SC₂H₅)butyl, 4-(n-propylthio)butyl or 4-(n-butylthio)butyl; in particular CH₂SCH₃ or (2-methylthio)ethyl;

C₁-C₄-haloalkylthio-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted by C₁-C₄-haloalkylthio as mentioned above, i.e. for example 2-(difluoromethylthio)ethyl, 2-(trifluoromethylthio)ethyl or 2-(pentafluoroethylthio)ethyl;

C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted by C₁-C₄-alkylsulfonyl as mentioned above, i.e. for example CH₂SO₂CH₃, CH₂SO₂C₂H₅, n-propylsulfonylmethyl, (1-methylethylsulfonyl)methyl, n-butylsulfonylmethyl, (1-methylpropylsulfonyl)methyl, (2-methylpropylsulfonyl)methyl, (1,1-dimethylethylsulfonyl)methyl, 2-methylsulfonylethyl, 2-ethylsulfonylethyl, 2-(n-propylsulfonyl)ethyl, 2-(1-methylethylsulfonyl)ethyl, 2-(n-butylsulfonyl)ethyl, 2-(1-methylpropylsulfonyl)ethyl, 2-(2-methylpropylsulfonyl)ethyl, 2-(1,1-dimethylethylsulfonyl)ethyl, 2-(SO₂CH₃)propyl, 3-(SO₂CH₃)propyl, 2-(SO₂C₂H₅)propyl, 3-(SO₂C₂H₅)propyl, 3-(propylsulfonyl)propyl, 3-(butylsulfonyl)propyl, 4-(SO₂CH₃)butyl, 4-(SO₂C₂H₅)butyl, 4-(n-propylsulfonyl)butyl or 4-(n-butylsulfonyl)butyl; in particular 2-(SO₂CH₃)ethyl or 2-(SO2C₂H₅)ethyl;

C₁-C₄-haloalkylsulfonyl-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted by C₁-C₄-haloalkylsulfonyl as mentioned above, i.e. for example 2-(2,2,2-trifluoroethylsulfonyl)ethyl;

(C₁-C₄-alkyl)carbonyl: COCH₃, COC₂H₅, n-propylcarbonyl, COCH(CH₃)₂, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or COC(CH₃)₃; in particular COCH₃, COC₂H₅ or COC(CH₃)₃;

(C₁-C₄-haloalkyl)carbonyl: (C₁-C₄-alkyl)carbonyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example COCH₂Cl, COCH(Cl)₂, COC(Cl)₃, COCH₂F, COCHF₂, COCF₃ COCHFCl, COCF(Cl)₂, COCF₂Cl, COCF₂Br, 1-fluoroethylcarbonyl, 2-fluoroethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 1,2-dichloroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, COC₂F₅, 3-chloropropylcarbonyl, heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl, 1-(chloromethyl)-2-chloroethylcarbonyl, 1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl; in particular COCH₂Cl, COCH₂F, COCHF₂, COCF₃, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 1,2-dichloroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl or COC₂F₅;

C₁-C₄-alkylcarbonyloxy: O—COCH₃, O—COC₂H₅, n-propyl-carbonyloxy, O—COCH(CH₃)₂, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or O—COC(CH₃)₃; in particular O—COCH₃, O—COC₂H₅ or O—COC(CH₃)₃;

(C₁-C₄-haloalkyl)carbonyloxy: (C₁-C₄-alkyl)carbonyloxy as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example O—COCH₂Cl, )—COCH(Cl)₂, O—COC(Cl)₃, O—COCH₂F, O—COCHF₂, O—COCF₃, O—COCHFCl, O—COCF(Cl)₂, O—COCF₂Cl, O—COCF₂Br, 1-fluoroethylcarbonyloxy, 2-fluoroethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2,2-difluoroethylcarbonyloxy, 2,2-dichloro-2-fluoroethylcarbonyloxy, 1,2-dichloroethylcarbonyloxy, 2,2,2tri-chloroethylcarbonyloxy, O—COC₂F₅, 3-chloropropylcarbonyloxy, heptafluoropropylcarbonyloxy, 1-(fluoromethyl)-2-fluoroethylcarbonyloxy, 1-(chloromethyl)-2-chloroethylcarbonyloxy, 1-(bromomethyl)-2-bromoethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutylcarbonyloxy or nonafluorobutylcarbonyloxy; in particular O—COCH₂Cl, O—COCH₂F, O—COCHF₂, O—COCF₃, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 1,2-dichloroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy or O—COC₂F₅;

(C₁-C₄-alkoxy)carbonyl and the alkoxycarbonyl radicals of alkoxycarbonylalkoxy: COOCH₃, COOC₂H₅, n-propoxycarbonyl, COOCH(CH₃)₂, n-butoxycarbonyl, 1-(methylpropoxy)carbonyl, 2-(methylpropoxy)carbonyl or COOC(CH₃)₃; in particular COOCH₃, COOC₂H₅ or COOC(CH₃)₃;

C₃-C₆-alkenyl and the alkenyl radicals of alkenyloxy: prop-1-en-1-yl, prop-2-en-1-yl, 1-methyl- ethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1, 3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl; in particular allyl or 2-buten-1-yl;

C₂-C₆-alkenyl: C₃-C₆-alkenyl as mentioned above and ethenyl;

C₃-C₆-haloalkenyl: C₃-C₆-alkenyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl; in particular 2-chloroallyl, 3-chloroallyl or 3,3-dichloroallyl;

C₂-C₆-haloalkenyl: C₃-C₆-haloalkenyl as mentioned above and 2-C1-ethenyl;

cyano-C₃-C₆-alkenyl: for example 2-cyanoallyl, 3-cyanoallyl, 4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5-cyanopent-4-enyl in particular 3-cyanoallyl or 4-cyanobut-2-enyl;

C₃—C₆-alkynyl and the alkynyl radicals of alkynyloxy: prop-1-yn-1-yl, propargyl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-yn-3-yl, 3-methylbut-r-yn-4-ylg n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2 -yn-4 -yl, n-hex-2-yn-5-yl, n-hex-2-yn-6 -yl, n-hex-3-yn-1-yl, n-hex-3-yn-2 -yl, 3-methyl-pent-1-yn-1-yl, 3-methyl-pent-1-yn-3-yl, 3-methyl-pent-1-yn-4-yl, 3-methyl-pent-1-yn-5-yl, 4-methyl-pent-1-yn-1-yl, 4-methyl-pent-2-yn-4-yl or 4-methyl-pent-2-yn-5-yl; in particular propargyl

3- to 7-membered heterocyclyl is a saturated, partially or fully unsaturated or aromatic heterocycle having one to three hetero atoms selected from a group consisting of

one to three nitrogen atoms,

one or two oxygen atoms and

one or two sulfur atoms.

Examples of saturated heterocycles which may contain a carbonyl or thiocarbonyl ring member are: oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diaziridin-3-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl, 1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydropyran-2-yl, tetrahydro-pyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydropyran-4-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl, hexahydro-1,3, 5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl, oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl, 1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-4-yl, 1,3-dithiepan-5-yl, 1,3-dithiepan-6-yl, 1,4-dioxepan-2-yl, 1,4-dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl, hexahydroazepin-3-yl, hexahydroazepin-4-yl, hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl, hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl and hexahydro-1,4-diazepin-2-yl;

Examples of unsaturated heterocycles which may contain a carbonyl or thiocarbonyl ring member are:

dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1,3-oxazolin-2-yl;

Preferred heteroaromatics are the 5- and 6-membered heteroaromatics, i.e. for example furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl, thiadiazolyl such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-2-yl, triazolyl such as 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl such as 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl; in particular pyridyl, pyrimidyl, furanyl and thienyl.

With a view to the use as herbicies, preference is given to those substituted tetrazolinonecarboxamides of the formula I where the variables have the following meaning, in each case either alone or in combination:

Het is tetrahydrofuran-3-yl, furan-3-yl, 2,4-dimethylfuran-3-yl, tetrahydrothiophen-3-yl, thiophen-3-yl, 2,4-dimethylthiophen-3-yl, tetra-hydro-2H-pyran-3-yl, tetrahydro-2H-thiopyran-3-yl, tetra-hydro-2H-pyran-4-yl or tetrahydro-2H-thiopyran-4-yl; particularly preferably tetrahydrofuran-3-yl, tetrahydrothiophen-3-yl, tetrahydro-2H-pyran-3-yl, tetrahydro-2H-thiopyran-3-yl, tetrahydro-2H-pyran-4-yl or tetrahydro-2H-thiopyran-4-yl;

R¹ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₄-haloalkylsulfonyl-C₁-C₄-alkyl, C₃-C₆-alkenyl, cyano-C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₅-C₈-cycloalkenyl, C₅ -C₈-cycloalkenyl-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, 3- to 7-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C₁-C₄-alkyl which may contain a carbonyl or thiocarbonyl ring member,

where the cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings may in each case be unsubstituted or may carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkylcarbonyloxy and C₁-C₄-haloalkylcarbonyloxy,

particularly preferably C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₄-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₅-C₈-cycloalkenyl, C₅-C₈-cycloalkenyl-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, 3- to 7-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C₁-C₄-alkyl which may contain a carbonyl or thiocarbonyl ring member,

where the cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings are in each case unsubstituted or may carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl or C₁-C₄-alkylcarbonyl;

particularly preferably C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, phenyl, phenyl-C₁-C₄-alkyl or C₃-C₇-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member,

where the cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings may in each case be unsubstituted or may carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl or C₁-C₄-alkylcarbonyl;

most particularly preferably C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, phenyl or C₃-C₇-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member,

where the cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings may in each case be unsubstituted or may carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl or C₁-C₄-alkylcarbonyl;

most particularly preferably phenyl which is unsubstituted or carries one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-halo-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl or C₁-C₄-alkylcarbonyl; in particular the substituents Xn listed individually in Table 1;

likewise most particularly preferred are the definitions listed individually for R¹ in Table 2;

R² is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, phenyl or benzyl; particularly preferably C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, phenyl or benzyl;

particularly preferably the definitions listed individually for R² in Tables 1 and 2.

Very particular preference is given to the compounds Ia (=I where Het=tetrahydro-2H-pyran-4-yl and R¹=phenyl with or without substitution) listed in Table 1 below

TABLE 1 Ia

No. X_(n) R² Ia.1 H CH₃ Ia.2 H C₂H₅ Ia.3 H n-C₃H₇ Ia.4 H i-C₃H₇ Ia.5 H n-C₄H₉ Ia.6 H CH₂—CH═CH₂ Ia.7 H CH₂—C≡CH Ia.8 H phenyl Ia.9 H benzyl Ia.10 2-F CH₃ Ia.11 2-F C₂H₅ Ia.12 2-F n-C₃H₇ Ia.13 2-F i-C₃H₇ Ia.14 2-F n-C₄H₉ Ia.15 2-F CH₂—CH═CH₂ Ia.16 2-F CH₂—C≡CH Ia.17 2-F phenyl Ia.18 2-F benzyl Ia.19 2-Cl CH₃ Ia.20 2-Cl C₂H₅ Ia.21 2-Cl n-C₃H₇ Ia.22 2-Cl i-C₃H₇ Ia.23 2-Cl n-C₄H₉ Ia.24 2-Cl CH₂—CH═CH₂ Ia.25 2-Cl CH₂—C≡CH Ia.26 2-Cl phenyl Ia.27 2-Cl benzyl Ia.28 2-Br CH₃ Ia.29 2-Br C₂H₅ Ia.30 2-Br n-C₃H₇ Ia.31 2-Br i-C₃H₇ Ia.32 2-Br n-C₄H₉ Ia.33 2-Br CH₂—CH═CH₂ Ia.34 2-Br CH₂—C≡CH Ia.35 2-Br phenyl Ia.36 2-Br benzyl Ia.37 2-CH₃ CH₃ Ia.38 2-CH₃ C₂H₅ Ia.39 2-CH₃ n-C₃H₇ Ia.40 2-CH₃ i-C₃H₇ Ia.41 2-CH₃ n-C₄H₉ Ia.42 2-CH₃ CH₂—CH═CH₂ Ia.43 2-CH₃ CH₂—C≡CH Ia.44 2-CH₃ phenyl Ia.45 2-CH₃ benzyl Ia.46 2-C₂H₅ CH₃ Ia.47 2-C₂H₅ C₂H₅ Ia.48 2-C₂H₅ n-C₃H₇ Ia.49 2-C₂H₅ i-C₃H₇ Ia.50 2-C₂H₅ n-C₄H₉ Ia.51 2-C₂H₅ CH₂—CH═CH₂ Ia.52 2-C₂H₅ CH₂—C≡CH Ia.53 2-C₂H₅ phenyl Ia.54 2-C₂H₅ benzyl Ia.55 2-OCH₃ CH₃ Ia.56 2-OCH₃ C₂H₅ Ia.57 2-OCH₃ n-C₃H₇ Ia.58 2-OCH₃ i-C₃H₇ Ia.59 2-OCH₃ n-C₄H₉ Ia.60 2-OCH₃ CH₂—CH═CH₂ Ia.61 2-OCH₃ CH₂—C≡CH Ia.62 2-OCH₃ phenyl Ia.63 2-OCH₃ benzyl Ia.64 2-OC₂H₅ CH₃ Ia.65 2-OC₂H₅ C₂H₅ Ia.66 2-OC₂H₅ n-C₃H₇ Ia.67 2-OC₂H₅ i-C₃H₇ Ia.68 2-OC₂H₅ n-C₄H₉ Ia.69 2-OC₂H₅ CH₂—CH═CH₂ Ia.70 2-OC₂H₅ CH₂—C≡CH Ia.71 2-OC₂H₅ phenyl Ia.72 2-OC₂H₅ benzyl Ia.73 2-SCH₃ CH₃ Ia.74 2-SCH₃ C₂H₅ Ia.75 2-SCH₃ n-C₃H₇ Ia.76 2-SCH₃ i-C₃H₇ Ia.77 2-SCH₃ n-C₄H₉ Ia.78 2-SCH₃ CH₂—CH═CH₂ Ia.79 2-SCH₃ CH₂—C≡CH Ia.80 2-SCH₃ phenyl Ia.81 2-SCH₃ benzyl Ia.82 2-OCHF₂ CH₃ Ia.83 2-OCHF₂ C₂H₅ Ia.84 2-OCHF₂ n-C₃H₇ Ia.85 2-OCHF₂ i-C₃H₇ Ia.86 2-OCHF₂ n-C₄H₉ Ia.87 2-OCHF₂ CH₂—CH═CH₂ Ia.88 2-OCHF₂ CH₂—C≡CH Ia.89 2-OCHF₂ phenyl Ia.90 2-OCHF₂ benzyl Ia.91 2-OCF₃ CH₃ Ia.92 2-OCF₃ C₂H₅ Ia.93 2-OCF₃ n-C₃H₇ Ia.94 2-OCF₃ i-C₃H₇ Ia.95 2-OCF₃ n-C₄H₉ Ia.96 2-OCF₃ CH₂—CH═CH₂ Ia.97 2-OCF₃ CH₂—C≡CH Ia.98 2-OCF₃ phenyl Ia.99 2-OCF₃ benzyl Ia.100 2-SO₂CH₃ CH₃ Ia.101 2-SO₂CH₃ C₂H₅ Ia.102 2-SO₂CH₃ n-C₃H₇ Ia.103 2-SO₂CH₃ i-C₃H₇ Ia.104 2-SO₂CH₃ n-C₄H₉ Ia.105 2-SO₂CH₃ CH₂—CH═CH₂ Ia.106 2-SO₂CH₃ CH₂—C≡CH Ia.107 2-SO₂CH₃ phenyl Ia.108 2-SO₂CH₃ benzyl Ia.109 3-Cl CH₃ Ia.110 3-Cl C₂H₅ Ia.111 3-Cl n-C₃H₇ Ia.112 3-Cl i-C₃H₇ Ia.113 3-Cl n-C₄H₉ Ia.114 3-Cl CH₂—CH═CH₂ Ia.115 3-Cl CH₂—C≡CH Ia.116 3-Cl phenyl Ia.117 3-Cl benzyl Ia.118 4-Cl CH₃ Ia.119 4-Cl C₂H₅ Ia.120 4-Cl n-C₃H₇ Ia.121 4-Cl i-C₃H₇ Ia.122 4-Cl n-C₄H₉ Ia.123 4-Cl CH₂—CH═CH₂ Ia.124 4-Cl CH₂—C≡CH Ia.125 4-Cl phenyl Ia.126 4-Cl benzyl Ia.127 3-CH₃ CH₃ Ia.128 3-CH₃ C₂H₅ Ia.129 3-CH₃ n-C₃H₇ Ia.130 3-CH₃ i-C₃H₇ Ia.131 3-CH₃ n-C₄H₉ Ia.132 3-CH₃ CH₂—CH═CH₂ Ia.133 3-CH₃ CH₂—C≡CH Ia.134 3-CH₃ phenyl Ia.135 3-CH₃ benzyl Ia.136 4-CH₃ CH₃ Ia.137 4-CH₃ C₂H₅ Ia.138 4-CH₃ n-C₃H₇ Ia.139 4-CH₃ i-C₃H₇ Ia.140 4-CH₃ n-C₄H₉ Ia.141 4-CH₃ CH₂—CH═CH₂ Ia.142 4-CH₃ CH₂—C≡CH Ia.143 4-CH₃ phenyl Ia.144 4-CH₃ benzyl Ia.145 2,6-F₂ CH₃ Ia.146 2,6-F₂ C₂H₅ Ia.147 2,6-F₂ n-C₃H₇ Ia.148 2,6-F₂ i-C₃H₇ Ia.149 2,6-F₂ n-C₄H₉ Ia.150 2,6-F₂ CH₂—CH═CH₂ Ia.151 2,6-F₂ CH₂—C≡CH Ia.152 2,6-F₂ phenyl Ia.153 2,6-F₂ benzyl Ia.154 2,6-Cl₂ CH₃ Ia.155 2,6-Cl₂ C₂H₅ Ia.156 2,6-Cl₂ n-C₃H₇ Ia.157 2,6-Cl₂ i-C₃H₇ Ia.158 2,6-Cl₂ n-C₄H₉ Ia.159 2,6-Cl₂ CH₂—CH═CH₂ Ia.160 2,6-Cl₂ CH₂—C≡CH Ia.161 2,6-Cl₂ phenyl Ia.162 2,6-Cl₂ benzyl Ia.163 2,6-Br₂ CH₃ Ia.164 2,6-Br₂ C₂H₅ Ia.165 2,6-Br₂ n-C₃H₇ Ia.166 2,6-Br₂ i-C₃H₇ Ia.167 2,6-Br₂ n-C₄H₉ Ia.168 2,6-Br₂ CH₂—CH═CH₂ Ia.169 2,6-Br₂ CH₂—C≡CH Ia.170 2,6-Br₂ phenyl Ia.171 2,6-Br₂ benzyl Ia.172 2,6-(CH₃)₂ CH₃ Ia.173 2,6-(CH₃)₂ C₂H₅ Ia.174 2,6-(CH₃)₂ n-C₃H₇ Ia.175 2,6-(CH₃)₂ i-C₃H₇ Ia.176 2,6-(CH₃)₂ n-C₄H₉ Ia.177 2,6-(CH₃)₂ CH₂—CH═CH₂ Ia.178 2,6-(CH₃)₂ CH₂—C≡CH Ia.179 2,6-(CH₃)₂ phenyl Ia.180 2,6-(CH₃)₂ benzyl Ia.181 2-Cl, 6-Br CH₃ Ia.182 2-Cl, 6-Br C₂H₅ Ia.183 2-Cl, 6-Br n-C₃H₇ Ia.184 2-Cl, 6-Br i-C₃H₇ Ia.185 2-Cl, 6-Br n-C₄H₉ Ia.186 2-Cl, 6-Br CH₂—CH═CH₂ Ia.187 2-Cl, 6-Br CH₂—C≡CH Ia.188 2-Cl, 6-Br phenyl Ia.189 2-Cl, 6-Br benzyl Ia.190 2-Cl, 6-F CH₃ Ia.191 2-Cl, 6-F C₂H₅ Ia.192 2-Cl, 6-F n-C₃H₇ Ia.193 2-Cl, 6-F i-C₃H₇ Ia.194 2-Cl, 6-F n-C₄H₉ Ia.195 2-Cl, 6-F CH₂—CH═CH₂ Ia.196 2-Cl, 6-F CH₂—C≡CH Ia.197 2-Cl, 6-F phenyl Ia.198 2-Cl, 6-F benzyl Ia.199 2-Cl, 6-CH₃ CH₃ Ia.200 2-Cl, 6-CH₃ C₂H₅ Ia.201 2-Cl, 6-CH₃ n-C₃H₇ Ia.202 2-Cl, 6-CH₃ i-C₃H₇ Ia.203 2-Cl, 6-CH₃ n-C₄H₉ Ia.204 2-Cl, 6-CH₃ CH₂—CH═CH₂ Ia.205 2-Cl, 6-CH₃ CH₂—C≡CH Ia.206 2-Cl, 6-CH₃ phenyl Ia.207 2-Cl, 6-CH₃ benzyl Ia.208 2-Br, 6-CH₃ CH₃ Ia.209 2-Br, 6-CH₃ C₂H₅ Ia.210 2-Br, 6-CH₃ n-C₃H₇ Ia.211 2-Br, 6-CH₃ i-C₃H₇ Ia.212 2-Br, 6-CH₃ n-C₄H₉ Ia.213 2-Br, 6-CH₃ CH₂—CH═CH₂ Ia.214 2-Br, 6-CH₃ CH₂—C≡CH Ia.215 2-Br, 6-CH₃ phenyl Ia.216 2-Br, 6-CH₃ benzyl Ia.217 2-Br, 6-C₂H₅ CH₃ Ia.218 2-Br, 6-C₂H₅ C₂H₅ Ia.219 2-Br, 6-C₂H₅ n-C₃H₇ Ia.220 2-Br, 6-C₂H₅ i-C₃H₇ Ia.221 2-Br, 6-C₂H₅ n-C₄H₉ Ia.222 2-Br, 6-C₂H₅ CH₂—CH═CH₂ Ia.223 2-Br, 6-C₂H₅ CH₂—C≡CH Ia.224 2-Br, 6-C₂H₅ phenyl Ia.225 2-Br, 6-C₂H₅ benzyl Ia.226 3-Cl, 4-i-C₃H₇ CH₃ Ia.227 3-Cl, 4-i-C₃H₇ C₂H₅ Ia.228 3-Cl, 4-i-C₃H₇ n-C₃H₇ Ia.229 3-Cl, 4-i-C₃H₇ i-C₃H₇ Ia.230 3-Cl, 4-i-C₃H₇ n-C₄H₉ Ia.231 3-Cl, 4-i-C₃H₇ CH₂—CH═CH₂ Ia.232 3-Cl, 4-i-C₃H₇ CH₂—C≡CH Ia.233 3-Cl, 4-i-C₃H₇ phenyl Ia.234 3-Cl, 4-i-C₃H₇ benzyl Ia.235 3-Cl, 4-O-i-C₃H₇ CH₃ Ia.236 3-Cl, 4-O-i-C₃H₇ C₂H₅ Ia.237 3-Cl, 4-O-i-C₃H₇ n-C₃H₇ Ia.238 3-Cl, 4-O-i-C₃H₇ i-C₃H₇ Ia.239 3-Cl, 4-O-i-C₃H₇ n-C₄H₉ Ia.240 3-Cl, 4-O-i-C₃H₇ CH₂—CH═CH₂ Ia.241 3-Cl, 4-O-i-C₃H₇ CH₂—C≡CH Ia.242 3-Cl, 4-O-i-C₃H₇ phenyl Ia.243 3-Cl, 4-O-i-C₃H₇ benzyl Ia.244 3-Cl, 4-CH₃ CH₃ Ia.245 3-Cl, 4-CH₃ C₂H₅ Ia.246 3-Cl, 4-CH₃ n-C₃H₇ Ia.247 3-Cl, 4-CH₃ i-C₃H₇ Ia.248 3-Cl, 4-CH₃ n-C₄H₉ Ia.249 3-Cl, 4-CH₃ CH₂—CH═CH₂ Ia.250 3-Cl, 4-CH₃ CH₂—C≡CH Ia.251 3-Cl, 4-CH₃ phenyl Ia.252 3-Cl, 4-CH₃ benzyl Ia.253 3-Cl, 4-CF₃ CH₃ Ia.254 3-Cl, 4-CF₃ C₂H₅ Ia.255 3-Cl, 4-CF₃ n-C₃H₇ Ia.256 3-Cl, 4-CF₃ i-C₃H₇ Ia.257 3-Cl, 4-CF₃ n-C₄H₉ Ia.258 3-Cl, 4-CF₃ CH₂—CH═CH₂ Ia.259 3-Cl, 4-CF₃ CH₂—C≡CH Ia.260 3-Cl, 4-CF₃ phenyl Ia.261 3-Cl, 4-CF₃ benzyl Ia.262 3-Cl, 4-OCF₃ CH₃ Ia.263 3-Cl, 4-OCF₃ C₂H₅ Ia.264 3-Cl, 4-OCF₃ n-C₃H₇ Ia.265 3-Cl, 4-OCF₃ i-C₃H₇ Ia.266 3-Cl, 4-OCF₃ n-C₄H₉ Ia.267 3-Cl, 4-OCF₃ CH₂—CH═CH₂ Ia.268 3-Cl, 4-OCF₃ CH₂—C≡CH Ia.269 3-Cl, 4-OCF₃ phenyl Ia.270 3-Cl, 4-OCF₃ benzyl Ia.271 3-Cl, 4-SCF₃ CH₃ Ia.272 3-Cl, 4-SCF₃ C₂H₅ Ia.273 3-Cl, 4-SCF₃ n-C₃H₇ Ia.274 3-Cl, 4-SCF₃ i-C₃H₇ Ia.275 3-Cl, 4-SCF₃ n-C₄H₉ Ia.276 3-Cl, 4-SCF₃ CH₂—CH═CH₂ Ia.277 3-Cl, 4-SCF₃ CH₂—C≡CH Ia.278 3-Cl, 4-SCF₃ phenyl Ia.279 3-Cl, 4-SCF₃ benzyl Ia.280 3-Br, 4-CH₃ CH₃ Ia.281 3-Br, 4-CH₃ C₂H₅ Ia.282 3-Br, 4-CH₃ n-C₃H₇ Ia.283 3-Br, 4-CH₃ i-C₃H₇ Ia.284 3-Br, 4-CH₃ n-C₄H₉ Ia.285 3-Br, 4-CH₃ CH₂—CH═CH₂ Ia.286 3-Br, 4-CH₃ CH₂—C≡CH Ia.287 3-Br, 4-CH₃ phenyl Ia.288 3-Br, 4-CH₃ benzyl Ia.289 3-F, 4-CH₃ CH₃ Ia.290 3-F, 4-CH₃ C₂H₅ Ia.291 3-F, 4-CH₃ n-C₃H₇ Ia.292 3-F, 4-CH₃ i-C₃H₇ Ia.293 3-F, 4-CH₃ n-C₄H₉ Ia.294 3-F, 4-CH₃ CH₂—CH═CH₂ Ia.295 3-F, 4-CH₃ CH₂—C≡CH Ia.296 3-F, 4-CH₃ phenyl Ia.297 3-F, 4-CH₃ benzyl Ia.298 2,3-Cl₂ CH₃ Ia.299 2,3-Cl₂ C₂H₅ Ia.300 2,3-Cl₂ n-C₃H₇ Ia.301 2,3-Cl₂ i-C₃H₇ Ia.302 2,3-Cl₂ n-C₄H₉ Ia.303 2,3-Cl₂ CH₂—CH═CH₂ Ia.304 2,3-Cl₂ CH₂—C≡CH Ia.305 2,3-Cl₂ phenyl Ia.306 2,3-Cl₂ benzyl Ia.307 2,4-Cl₂ CH₃ Ia.308 2,4-Cl₂ C₂H₅ Ia.309 2,4-Cl₂ n-C₃H₇ Ia.310 2,4-Cl₂ i-C₃H₇ Ia.311 2,4-Cl₂ n-C₄H₉ Ia.312 2,4-Cl₂ CH₂—CH═CH₂ Ia.313 2,4-Cl₂ CH₂—C≡CH Ia.314 2,4-Cl₂ phenyl Ia.315 2,4-Cl₂ benzyl Ia.316 2,5-Cl₂ CH₃ Ia.317 2,5-Cl₂ C₂H₅ Ia.318 2,5-Cl₂ n-C₃H₇ Ia.319 2,5-Cl₂ i-C₃H₇ Ia.320 2,5-Cl₂ n-C₄H₉ Ia.321 2,5-Cl₂ CH₂—CH═CH₂ Ia.322 2,5-Cl₂ CH₂—C≡CH Ia.323 2,5-Cl₂ phenyl Ia.324 2,5-Cl₂ benzyl Ia.325 2,3-(CH₃)₂ CH₃ Ia.326 2,3-(CH₃)₂ C₂H₅ Ia.327 2,3-(CH₃)₂ n-C₃H₇ Ia.328 2,3-(CH₃)₂ i-C₃H₇ Ia.329 2,3-(CH₃)₂ n-C₄H₉ Ia.330 2,3-(CH₃)₂ CH₂—CH═CH₂ Ia.331 2,3-(CH₃)₂ CH₂—C≡CH Ia.332 2,3-(CH₃)₂ phenyl Ia.333 2,3-(CH₃)₂ benzyl Ia.334 2,4-(CH₃)₂ CH₃ Ia.335 2,4-(CH₃)₂ C₂H₅ Ia.336 2,4-(CH₃)₂ n-C₃H₇ Ia.337 2,4-(CH₃)₂ i-C₃H₇ Ia.338 2,4-(CH₃)₂ n-C₄H₉ Ia.339 2,4-(CH₃)₂ CH₂—CH═CH₂ Ia.340 2,4-(CH₃)₂ CH₂—C≡CH Ia.341 2,4-(CH₃)₂ phenyl Ia.342 2,4-(CH₃)₂ benzyl Ia.343 2,5-(CH₃)₂ CH₃ Ia.344 2,5-(CH₃)₂ C₂H₅ Ia.345 2,5-(CH₃)₂ n-C₃H₇ Ia.346 2,5-(CH₃)₂ i-C₃H₇ Ia.347 2,5-(CH₃)₂ n-C₄H₉ Ia.348 2,5-(CH₃)₂ CH₂—CH═CH₂ Ia.349 2,5-(CH₃)₂ CH₂—C≡CH Ia.350 2,5-(CH₃)₂ phenyl Ia.351 2,5-(CH₃)₂ benzyl Ia.352 2,3-(OCH₃)₂ CH₃ Ia.353 2,3-(OCH₃)₂ C₂H₅ Ia.354 2,3-(OCH₃)₂ n-C₃H₇ Ia.355 2,3-(OCH₃)₂ i-C₃H₇ Ia.356 2,3-(OCH₃)₂ n-C₄H₉ Ia.357 2,3-(OCH₃)₂ CH₂—CH═CH₂ Ia.358 2,3-(OCH₃)₂ CH₂—C≡CH Ia.359 2,3-(OCH₃)₂ phenyl Ia.360 2,3-(OCH₃)₂ benzyl Ia.361 2,4-(OCH₃)₂ CH₃ Ia.362 2,4-(OCH₃)₂ C₂H₅ Ia.363 2,4-(OCH₃)₂ n-C₃H₇ Ia.364 2,4-(OCH₃)₂ i-C₃H₇ Ia.365 2,4-(OCH₃)₂ n-C₄H₉ Ia.366 2,4-(OCH₃)₂ CH₂—CH═CH₂ Ia.367 2,4-(OCH₃)₂ CH₂—C≡CH Ia.368 2,4-(OCH₃)₂ phenyl Ia.369 2,4-(OCH₃)₂ benzyl Ia.370 2,5-(OCH₃)₂ CH₃ Ia.371 2,5-(OCH₃)₂ C₂H₅ Ia.372 2,5-(OCH₃)₂ n-C₃H₇ Ia.373 2,5-(OCH₃)₂ i-C₃H₇ Ia.374 2,5-(OCH₃)₂ n-C₄H₉ Ia.375 2,5-(OCH₃)₂ CH₂—CH═CH₂ Ia.376 2,5-(OCH₃)₂ CH₂—C≡CH Ia.377 2,5-(OCH₃)₂ phenyl Ia.378 2,5-(OCH₃)₂ benzyl Ia.379 2,6-(OCH₃)₂ CH₃ Ia.380 2,6-(OCH₃)₂ C₂H₅ Ia.381 2,6-(OCH₃)₂ n-C₃H₇ Ia.382 2,6-(OCH₃)₂ i-C₃H₇ Ia.383 2,6-(OCH₃)₂ n-C₄H₉ Ia.384 2,6-(OCH₃)₂ CH₂—CH═CH₂ Ia.385 2,6-(OCH₃)₂ CH₂—C≡CH Ia.386 2,6-(OCH₃)₂ phenyl Ia.387 2,6-(OCH₃)₂ benzyl Ia.388 2-CF₃ CH₃ Ia.389 2-CF₃ C₂H₅ Ia.390 2-CF₃ n-C₃H₇ Ia.391 2-CF₃ i-C₃H₇ Ia.392 2-CF₃ n-C₄H₉ Ia.393 2-CF₃ CH₂—CH═CH₂ Ia.394 2-CF₃ CH₂—C≡CH Ia.395 2-CF₃ phenyl Ia.396 2-CF₃ benzyl

Furthermore, particular preference is given to the substituted tetrazolinonecarboxamides below:

The compounds Ib.1-Ib.396 which differ from the corresponding compounds Ia.1-Ia.396 only in that Het is tetrahydrofuran-3-yl:

The compounds Ic.1-Ic.396, which differ from the corresponding compounds Ia.1-Ia.396 only in that Het is furan-3-yl:

The compounds Id.1-Id.396 which differ from the corresponding compounds Ia.1-Ia.396 only in that Het is 2,4-dimethylfuran-3-yl:

The compounds Ie.1-Ie.396 which differ from the corresponding compounds Ia.1-Ia.396 only in that Het is tetrahydro-2H-thio-pyran-4-yl:

The compounds If.1-Id.396 which differ from the corresponding compounds Ia.1-Ia.396 only in that Het is tetrahydrothiophen-3-yl:

The compounds Ig.1-Ig.396 which differ from the corresponding compounds Ia.1-Ia.396 in that Het is thiophen-3-yl:

The compounds Ih.1-Ih.396 which differ from the corresponding compounds Ia.1-Ia.396 in that Het is 2,4-dimethylthiophen-3-yl:

Moreover, very particular preference is given to the compounds Ii (=I where Het=tetrahydro-2H-pyran-4-yl) listed in Table 2 below:

TABLE 2 Ii

No. R¹ R² Ii.1 CH₃ CH₃ Ii.2 CH₃ C₂H₅ Ii.3 CH₃ n-C₃H₇ Ii.4 CH₃ i-C₃H₇ Ii.5 CH₃ n-C₄H₉ Ii.6 CH₃ CH₂—CH═CH₂ Ii.7 CH₃ CH₂—C≡CH Ii.8 CH₃ phenyl Ii.9 CH₃ benzyl Ii.10 C₂H₅ CH₃ Ii.11 C₂H₅ C₂H₅ Ii.12 C₂H₅ n-C₃H₇ Ii.13 C₂H₅ i-C₃H₇ Ii.14 C₂H₅ n-C₄H₉ Ii.15 C₂H₅ CH₂—CH═CH₂ Ii.16 C₂H₅ CH₂—C≡CH Ii.17 C₂H₅ phenyl Ii.18 C₂H₅ benzyl Ii.19 n-C₃H₇ CH₃ Ii.20 n-C₃H₇ C₂H₅ Ii.21 n-C₃H₇ n-C₃H₇ Ii.22 n-C₃H₇ i-C₃H₇ Ii.23 n-C₃H₇ n-C₄H₉ Ii.24 n-C₃H₇ CH₂—CH═CH₂ Ii.25 n-C₃H₇ CH₂—C≡CH Ii.26 n-C₃H₇ phenyl Ii.27 n-C₃H₇ benzyl Ii.28 i-C₃H₇ CH₃ Ii.29 i-C₃H₇ C₂H₅ Ii.30 i-C₃H₇ n-C₃H₇ Ii.31 i-C₃H₇ i-C₃H₇ Ii.32 i-C₃H₇ n-C₄H₉ Ii.33 i-C₃H₇ CH₂—CH═CH₂ Ii.34 i-C₃H₇ CH₂—C≡CH Ii.35 i-C₃H₇ phenyl Ii.36 i-C₃H₇ benzyl Ii.37 n-C₄H₉ CH₃ Ii.38 n-C₄H₉ C₂H₅ Ii.39 n-C₄H₉ n-C₃H₇ Ii.40 n-C₄H₉ i-C₃H₇ Ii.41 n-C₄H₉ n-C₄H₉ Ii.42 n-C₄H₉ CH₂—CH═CH₂ Ii.43 n-C₄H₉ CH₂—C≡CH Ii.44 n-C₄H₉ phenyl Ii.45 n-C₄H₉ benzyl Ii.46 CH₂—CH₂—Cl CH₃ Ii.47 CH₂—CH₂—Cl C₂H₅ Ii.48 CH₂—CH₂—Cl n-C₃H₇ Ii.49 CH₂—CH₂—Cl i-C₃H₇ Ii.50 CH₂—CH₂—Cl n-C₄H₉ Ii.51 CH₂—CH₂—Cl CH₂—CH═CH₂ Ii.52 CH₂—CH₂—Cl CH₂—C≡CH Ii.53 CH₂—CH₂—Cl phenyl Ii.54 CH₂—CH₂—Cl benzyl Ii.55 CH₂—CF₃ CH₃ Ii.56 CH₂—CF₃ C₂H₅ Ii.57 CH₂—CF₃ n-C₃H₇ Ii.58 CH₂—CF₃ i-C₃H₇ Ii.59 CH₂—CF₃ n-C₄H₉ Ii.60 CH₂—CF₃ CH₂—CH═CH₂ Ii.61 CH₂—CF₃ CH₂—C≡CH Ii.62 CH₂—CF₃ phenyl Ii.63 CH₂—CF₃ benzyl Ii.64 CH═CH₂ CH₃ Ii.65 CH═CH₂ C₂H₅ Ii Ii.78 CH₂—CH═CH₂ CH₂—CH═CH₂ Ii.79 CH₂—CH═CH₂ CH₂—C≡CH Ii.80 CH₂—CH═CH₂ phenyl Ii.81 CH₂—CH═CH₂ benzyl Ii.82 CH═CH—CH₃ CH₃ Ii.83 CH═CH—CH₃ C₂H₅ Ii.84 CH═CH—CH₃ n-C₃H₇ Ii.85 CH═CH—CH₃ i-C₃H₇ Ii.86 CH═CH—CH₃ n-C₄H₉ Ii.87 CH═CH—CH₃ CH₂—CH═CH₂ Ii.88 CH═CH—CH₃ CH₂—C≡CH Ii.89 CH═CH—CH₃ phenyl Ii.90 CH═CH—CH₃ benzyl Ii.91 CH═CH—Cl CH₃ Ii.92 CH═CH—Cl C₂H₅ Ii.93 CH═CH—Cl n-C₃H₇ Ii.94 CH═CH—Cl i-C₃H₇ Ii.95 CH═CH—Cl n-C₄H₉ Ii.96 CH═CH—Cl CH₂—CH═CH₂ Ii.97 CH═CH—Cl CH₂—C≡CH Ii.98 CH═CH—Cl Ii.112 1-methylcyclopropyl i-C₃H₇ Ii.113 1-methylcyclopropyl n-C₄H₉ Ii.114 1-methylcyclopropyl CH₂—CH═CH₂ Ii.115 1-methylcyclopropyl CH₂—C≡CH Ii.116 1-methylcyclopropyl phenyl Ii.117 1-methylcyclopropyl benzyl Ii.118 2-methylcyclopropyl CH₃ Ii.119 2-methylcyclopropyl C₂H₅ Ii.120 2-methylcyclopropyl n-C₃H₇ Ii.121 2-methylcyclopropyl i-C₃H₇ Ii.122 2-methylcyclopropyl n-C₄H₉ Ii.123 2-methylcyclopropyl CH₂—CH═CH₂ Ii.124 2-methylcyclopropyl CH₂—C≡CH Ii.125 2-methylcyclopropyl phenyl Ii.126 2-methylcyclopropyl benzyl Ii.127 2,2-dichlorocyclopropyl CH₃ Ii.128 2,2-dichlorocyclopropyl C₂H₅ Ii.129 2,2-dichlorocyclopropyl n-C₃H₇ Ii.130 2,2-dichlorocyclopropyl i-C₃H₇ Ii.131 2,2-dichlorocyclopropyl n-C₄H₉ Ii.132 2,2-dichlorocyclopropyl CH₂—CH═CH₂ Ii.133 2,2-dichlorocyclopropyl CH₂—C≡CH Ii.134 2,2-dichlorocyclopropyl phenyl Ii.135 2,2-dichlorocyclopropyl benzyl Ii.136 2,2-difluorocyclopropyl CH₃ Ii.137 2,2-difluorocyclopropyl C₂H₅ Ii.138 2,2-difluorocyclopropyl n-C₃H₇ Ii.139 2,2-difluorocyclopropyl i-C₃H₇ Ii.140 2,2-difluorocyclopropyl n-C₄H₉ Ii.141 2,2-difluorocyclopropyl CH₂—CH═CH₂ Ii.142 2,2-difluorocyclopropyl CH₂—C≡CH Ii.143 2,2-difluorocyclopropyl phenyl Ii.144 2,2-difluorocyclopropyl benzyl Ii.145 2,2-difluoro-1-methylcyclopropyl CH₃ Ii.146 2,2-difluoro-1-methylcyclopropyl C₂H₅ Ii.147 2,2-difluoro-1-methylcyclopropyl n-C₃H₇ Ii.148 2,2-difluoro-1-methylcyclopropyl i-C₃H₇ Ii.149 2,2-difluoro-1-methylcyclopropyl n-C₄H₉ Ii.150 2,2-difluoro-1-methylcyclopropyl CH₂—CH═CH₂ Ii.151 2,2-difluoro-1-methylcyclopropyl CH₂—C≡CH Ii.152 2,2-difluoro-1-methylcyclopropyl phenyl Ii.153 2,2-difluoro-1-methylcyclopropyl benzyl Ii.154 2,2-dichloro-1-methylcyclopropyl CH₃ Ii.155 2,2-dichloro-1-methylcyclopropyl C₂H₅ Ii.156 2,2-dichloro-1-methylcyclopropyl n-C₃H₇ Ii.157 2,2-dichloro-1-methylcyclopropyl i-C₃H₇ Ii.158 2,2-dichloro-1-methylcyclopropyl n-C₄H₉ Ii.159 2,2-dichloro-1-methylcyclopropyl CH₂—CH═CH₂ Ii.160 2,2-dichloro-1-methylcyclopropyl CH₂—C≡CH Ii.161 2,2-dichloro-1-methylcyclopropyl phenyl Ii.162 2,2-dichloro-1-methylcyclopropyl benzyl Ii.163 cyclobutyl CH₃ Ii.164 cyclobutyl C₂H₅ Ii.165 cyclobutyl n-C₃H₇ Ii.166 cyclobutyl i-C₃H₇ Ii.167 cyclobutyl n-C₄H₉ Ii.168 cyclobutyl CH₂—CH═CH₂ Ii.169 cyclobutyl CH₂—C≡CH Ii.170 cyclobutyl phenyl Ii.171 cyclobutyl benzyl Ii.172 1-methylcyclobutyl CH₃ Ii.173 1-methylcyclobutyl C₂H₅ Ii.174 1-methylcyclobutyl n-C₃H₇ Ii.175 1-methylcyclobutyl i-C₃H₇ Ii.176 1-methylcyclobutyl n-C₄H₉ Ii.177 1-methylcyclobutyl CH₂—CH═CH₂ Ii.178 1-methylcyclobutyl CH₂—C≡CH Ii.179 1-methylcyclobutyl phenyl Ii.180 1-methylcyclobutyl benzyl Ii.181 cyclopentyl CH₃ Ii.182 cyclopentyl C₂H₅ Ii.183 cyclopentyl n-C₃H₇ Ii.184 cyclopentyl i-C₃H₇ Ii.185 cyclopentyl n-C₄H₉ Ii.186 cyclopentyl CH₂—CH═CH₂ Ii.187 cyclopentyl CH₂—C≡CH Ii.188 cyclopentyl phenyl Ii.189 cyclopentyl benzyl Ii.190 1-methylcyclopentyl CH₃ Ii.191 1-methylcyclopentyl C₂H₅ Ii.192 1-methylcyclopentyl n-C₃H₇ Ii.193 1-methylcyclopentyl i-C₃H₇ Ii.194 1-methylcyclopentyl n-C₄H₉ Ii.195 1-methylcyclopentyl CH₂—CH═CH₂ Ii.196 1-methylcyclopentyl CH₂—C≡CH Ii.197 1-methylcyclopentyl phenyl Ii.198 1-methylcyclopentyl benzyl Ii.199 cyclohexyl CH₃ Ii.200 cyclohexyl C₂H₅ Ii.201 cyclohexyl n-C₃H₇ Ii.202 cyclohexyl i-C₃H₇ Ii.203 cyclohexyl n-C₄H₉ Ii.204 cyclohexyl CH₂—CH═CH₂ Ii.205 cyclohexyl CH₂—C≡CH Ii.206 cyclohexyl phenyl Ii.207 cyclohexyl benzyl Ii.208 1-methylcyclohexyl CH₃ Ii.209 1-methylcyclohexyl C₂H₅ Ii.210 1-methylcyclohexyl n-C₃H₇ Ii.211 1-methylcyclohexyl i-C₃H₇ Ii.212 1-methylcyclohexyl n-C₄H₉ Ii.213 1-methylcyclohexyl CH₂—CH═CH₂ Ii.214 1-methylcyclohexyl CH₂—C≡CH Ii.215 1-methylcyclohexyl phenyl Ii.216 1-methylcyclohexyl benzyl Ii.217 2-methylcyclohexyl CH₃ Ii.218 2-methylcyclohexyl C₂H₅ Ii.219 2-methylcyclohexyl n-C₃H₇ Ii.220 2-methylcyclohexyl i-C₃H₇ Ii.221 2-methylcyclohexyl n-C₄H₉ Ii.222 2-methylcyclohexyl CH₂—CH═CH₂ Ii.223 2-methylcyclohexyl CH₂—C≡CH Ii.224 2-methylcyclohexyl phenyl Ii.225 2-methylcyclohexyl benzyl Ii.226 3-methylcyclohexyl CH₃ Ii.227 3-methylcyclohexyl C₂H₅ Ii.228 3-methylcyclohexyl n-C₃H₇ Ii.229 3-methylcyclohexyl i-C₃H₇ Ii.230 3-methylcyclohexyl n-C₄H₉ Ii.231 3-methylcyclohexyl CH₂—CH═CH₂ Ii.232 3-methylcyclohexyl CH₂—C≡CH Ii.233 3-methylcyclohexyl phenyl Ii.234 3-methylcyclohexyl benzyl Ii.235 4-methylcyclohexyl CH₃ Ii.236 4-methylcyclohexyl C₂H₅ Ii.237 4-methylcyclohexyl n-C₃H₇ Ii.238 4-methylcyclohexyl i-C₃H₇ Ii.239 4-methylcyclohexyl n-C₄H₉ Ii.240 4-methylcyclohexyl CH₂—CH═CH₂ Ii.241 4-methylcyclohexyl CH₂—C≡CH Ii.242 4-methylcyclohexyl phenyl Ii.243 4-methylcyclohexyl benzyl Ii.244 2,3-dimethylcyclohexyl CH₃ Ii.245 2,3-dimethylcyclohexyl C₂H₅ Ii.246 2,3-dimethylcyclohexyl n-C₃H₇ Ii.247 2,3-dimethylcyclohexyl i-C₃H₇ Ii.248 2,3-dimethylcyclohexyl n-C₄H₉ Ii.249 2,3-dimethylcyclohexyl CH₂—CH═CH₂ Ii.250 2,3-dimethylcyclohexyl CH₂—C≡CH Ii.251 2,3-dimethylcyclohexyl phenyl Ii.252 2,3-dimethylcyclohexyl benzyl Ii.253 2,6-dimethylcyclohexyl CH₃ Ii.254 2,6-dimethylcyclohexyl C₂H₅ Ii.255 2,6-dimethylcyclohexyl n-C₃H₇ Ii.256 2,6-dimethylcyclohexyl i-C₃H₇ Ii.257 2,6-dimethylcyclohexyl n-C₄H₉ Ii.258 2,6-dimethylcyclohexyl CH₂—CH═CH₂ Ii.259 2,6-dimethylcyclohexyl CH₂—C≡CH Ii.260 2,6-dimethylcyclohexyl phenyl Ii.261 2,6-dimethylcyclohexyl benzyl Ii.262 1-cyclopentenyl CH₃ Ii.263 1-cyclopentenyl C₂H₅ Ii.264 1-cyclopentenyl n-C₃H₇ Ii.265 1-cyclopentenyl i-C₃H₇ Ii.266 1-cyclopentenyl n-C₄H₉ Ii.267 1-cyclopentenyl CH₂—CH═CH₂ Ii.268 1-cyclopentenyl CH₂—C≡CH Ii.269 1-cyclopentenyl phenyl Ii.270 1-cyclopentenyl benzyl Ii.271 2-chloro-1-cyclopentenyl CH₃ Ii.272 2-chloro-1-cyclopentenyl C₂H₅ Ii.273 2-chloro-1-cyclopentenyl n-C₃H₇ Ii.274 2-chloro-1-cyclopentenyl i-C₃H₇ Ii.275 2-chloro-1-cyclopentenyl n-C₄H₉ Ii.276 2-chloro-1-cyclopentenyl CH₂—CH═CH₂ Ii.277 2-chloro-1-cyclopentenyl CH₂—C≡CH Ii.278 2-chloro-1-cyclopentenyl phenyl Ii.279 2-chloro-1-cyclopentenyl benzyl Ii.280 1-cyclohexenyl CH₃ Ii.281 1-cyclohexenyl C₂H₅ Ii.282 1-cyclohexenyl n-C₃H₇ Ii.283 1-cyclohexenyl i-C₃H₇ Ii.284 1-cyclohexenyl n-C₄H₉ Ii.285 1-cyclohexenyl CH₂—CH═CH₂ Ii.286 1-cyclohexenyl CH₂—C≡CH Ii.287 1-cyclohexenyl phenyl Ii.288 1-cyclohexenyl benzyl Ii.289 2-chloro-1-cyclohexenyl CH₃ Ii.290 2-chloro-1-cyclohexenyl C₂H₅ Ii.291 2-chloro-1-cyclohexenyl n-C₃H₇ Ii.292 2-chloro-1-cyclohexenyl i-C₃H₇ Ii.293 2-chloro-1-cyclohexenyl n-C₄H₉ Ii.294 2-chloro-1-cyclohexenyl CH₂—CH═CH₂ Ii.295 2-chloro-1-cyclohexenyl CH₂—C≡CH Ii.296 2-chloro-1-cyclohexenyl phenyl Ii.297 2-chloro-1-cyclohexenyl benzyl Ii.298 benzyl CH₃ Ii.299 benzyl C₂H₅ Ii.300 benzyl n-C₃H₇ Ii.301 benzyl i-C₃H₇ Ii.302 benzyl n-C₄H₉ Ii.303 benzyl CH₂—CH═CH₂ Ii.304 benzyl CH₂—C≡CH Ii.305 benzyl phenyl Ii.306 benzyl benzyl Ii.307 2-chlorobenzyl CH₃ Ii.308 2-chlorobenzyl C₂H₅ Ii.309 2-chlorobenzyl n-C₃H₇ Ii.310 2-chlorobenzyl i-C₃H₇ Ii.311 2-chlorobenzyl n-C₄H₉ Ii.312 2-chlorobenzyl CH₂—CH═CH₂ Ii.313 2-chlorobenzyl CH₂—C≡CH Ii.314 2-chlorobenzyl phenyl Ii.315 2-chlorobenzyl benzyl Ii.316 2-methylbenzyl CH₃ Ii.317 2-methylbenzyl C₂H₅ Ii.318 2-methylbenzyl n-C₃H₇ Ii.319 2-methylbenzyl i-C₃H₇ Ii.320 2-methylbenzyl n-C₄H₉ Ii.321 2-methylbenzyl CH₂—CH═CH₂ Ii.322 2-methylbenzyl CH₂—C≡CH Ii.323 2-methylbenzyl phenyl Ii.324 2-methylbenzyl benzyl Ii.325 2,6-dimethylbenzyl CH₃ Ii.326 2,6-dimethylbenzyl C₂H₅ Ii.327 2,6-dimethylbenzyl n-C₃H₇ Ii.328 2,6-dimethylbenzyl i-C₃H₇ Ii.329 2,6-dimethylbenzyl n-C₄H₉ Ii.330 2,6-dimethylbenzyl CH₂—CH═CH₂ Ii.331 2,6-dimethylbenzyl CH₂—C≡CH Ii.332 2,6-dimethylbenzyl phenyl Ii.333 2,6-dimethylbenzyl benzyl Ii.334 2,6-dichlorobenzyl CH₃ Ii.335 2,6-dichlorobenzyl C₂H₅ Ii.336 2,6-dichlorobenzyl n-C₃H₇ Ii.337 2,6-dichlorobenzyl i-C₃H₇ Ii.338 2,6-dichlorobenzyl n-C₄H₉ Ii.339 2,6-dichlorobenzyl CH₂—CH═CH₂ Ii.340 2,6-dichlorobenzyl CH₂—C≡CH Ii.341 2,6-dichlorobenzyl phenyl Ii.342 2,6-dichlorobenzyl benzyl Ii.343 2-methyl-3-furyl CH₃ Ii.344 2-methyl-3-furyl C₂H₅ Ii.345 2-methyl-3-furyl n-C₃H₇ Ii.346 2-methyl-3-furyl i-C₃H₇ Ii.347 2-methyl-3-furyl n-C₄H₉ Ii.348 2-methyl-3-furyl CH₂—CH═CH₂ Ii.349 2-methyl-3-furyl CH₂—C≡CH Ii.350 2-methyl-3-furyl phenyl Ii.351 2-methyl-3-furyl benzyl Ii.352 2,4-dimethyl-3-furyl CH₃ Ii.353 2,4-dimethyl-3-furyl C₂H₅ Ii.354 2,4-dimethyl-3-furyl n-C₃H₇ Ii.355 2,4-dimethyl-3-furyl i-C₃H₇ Ii.356 2,4-dimethyl-3-furyl n-C₄H₉ Ii.357 2,4-dimethyl-3-furyl CH₂—CH═CH₂ Ii.358 2,4-dimethyl-3-furyl CH₂—C≡CH Ii.359 2,4-dimethyl-3-furyl phenyl Ii.360 2,4-dimethyl-3-furyl benzyl Ii.361 2,5-dimethyl-3-furyl CH₃ Ii.362 2,5-dimethyl-3-furyl C₂H₅ Ii.363 2,5-dimethyl-3-furyl n-C₃H₇ Ii.364 2,5-dimethyl-3-furyl i-C₃H₇ Ii.365 2,5-dimethyl-3-furyl n-C₄H₉ Ii.366 2,5-dimethyl-3-furyl CH₂—CH═CH₂ Ii.367 2,5-dimethyl-3-furyl CH₂—C≡CH Ii.368 2,5-dimethyl-3-furyl phenyl Ii.369 2,5-dimethyl-3-furyl benzyl Ii.370 thiophen-2-yl CH₃ Ii.371 thiophen-2-yl C₂H₅ Ii.372 thiophen-2-yl n-C₃H₇ Ii.373 thiophen-2-yl i-C₃H₇ Ii.374 thiophen-2-yl n-C₄H₉ Ii.375 thiophen-2-yl CH₂—CH═CH₂ Ii.376 thiophen-2-yl CH₂—C≡CH Ii.377 thiophen-2-yl phenyl Ii.378 thiophen-2-yl benzyl Ii.379 thiophen-3-yl CH₃ Ii.380 thiophen-3-yl C₂H₅ Ii.381 thiophen-3-yl n-C₃H₇ Ii.382 thiophen-3-yl i-C₃H₇ Ii.383 thiophen-3-yl n-C₄H₉ Ii.384 thiophen-3-yl CH₂—CH═CH₂ Ii.385 thiophen-3-yl CH₂—C≡CH Ii.386 thiophen-3-yl phenyl Ii.387 thiophen-3-yl benzyl Ii.388 3-chlorothiophen-2-yl CH₃ Ii.389 3-chlorothiophen-2-yl C₂H₅ Ii.390 3-chlorothiophen-2-yl n-C₃H₇ Ii.391 3-chlorothiophen-2-yl i-C₃H₇ Ii.392 3-chlorothiophen-2-yl n-C₄H₉ Ii.393 3-chlorothiophen-2-yl CH₂—CH═CH₂ Ii.394 3-chlorothiophen-2-yl CH₂—C≡CH Ii.395 3-chlorothiophen-2-yl phenyl Ii.396 3-chlorothiophen-2-yl benzyl Ii.397 3-methylthiophen-2-yl CH₃ Ii.398 3-methylthiophen-2-yl C₂H₅ Ii.399 3-methylthiophen-2-yl n-C₃H₇ Ii.400 3-methylthiophen-2-yl i-C₃H₇ Ii.401 3-methylthiophen-2-yl n-C₄H₉ Ii.402 3-methylthiophen-2-yl CH₂—CH═CH₂ Ii.403 3-methylthiophen-2-yl CH₂—C≡CH Ii.404 3-methylthiophen-2-yl phenyl Ii.405 3-methylthiophen-2-yl benzyl Ii.406 5-chlorothiophen-2-yl CH₃ Ii.407 5-chlorothiophen-2-yl C₂H₅ Ii.408 5-chlorothiophen-2-yl n-C₃H₇ Ii.409 5-chlorothiophen-2-yl i-C₃H₇ Ii.410 5-chlorothiophen-2-yl n-C₄H₉ Ii.411 5-chlorothiophen-2-yl CH₂—CH═CH₂ Ii.412 5-chlorothiophen-2-yl CH₂—C≡CH Ii.413 5-chlorothiophen-2-yl phenyl Ii.414 5-chlorothiophen-2-yl benzyl Ii.415 1-methyl-2-pyrrolyl CH₃ Ii.416 1-methyl-2-pyrrolyl C₂H₅ Ii.417 1-methyl-2-pyrrolyl n-C₃H₇ Ii.418 1-methyl-2-pyrrolyl i-C₃H₇ Ii.419 1-methyl-2-pyrrolyl n-C₄H₉ Ii.420 1-methyl-2-pyrrolyl CH₂—CH═CH₂ Ii.421 1-methyl-2-pyrrolyl CH₂—C≡CH Ii.422 1-methyl-2-pyrrolyl phenyl Ii.423 1-methyl-2-pyrrolyl benzyl Ii.424 3,5-dimethyl-4-isoxazolyl CH₃ Ii.425 3,5-dimethyl-4-isoxazolyl C₂H₅ Ii.426 3,5-dimethyl-4-isoxazolyl n-C₃H₇ Ii.427 3,5-dimethyl-4-isoxazolyl i-C₃H₇ Ii.428 3,5-dimethyl-4-isoxazolyl n-C₄H₉ Ii.429 3,5-dimethyl-4-isoxazolyl CH₂—CH═CH₂ Ii.430 3,5-dimethyl-4-isoxazolyl CH₂—C≡CH Ii.431 3,5-dimethyl-4-isoxazolyl phenyl Ii.432 3,5-dimethyl-4-isoxazolyl benzyl Ii.433 5-methyl-3-isoxazolyl CH₃ Ii.434 5-methyl-3-isoxazolyl C₂H₅ Ii.435 5-methyl-3-isoxazolyl n-C₃H₇ Ii.436 5-methyl-3-isoxazolyl i-C₃H₇ Ii.437 5-methyl-3-isoxazolyl n-C₄H₉ Ii.438 5-methyl-3-isoxazolyl CH₂—CH═CH₂ Ii.439 5-methyl-3-isoxazolyl CH₂—C≡CH Ii.440 5-methyl-3-isoxazolyl phenyl Ii.441 5-methyl-3-isoxazolyl benzyl Ii.442 2,4-dimethyl-5-thiazolyl CH₃ Ii.443 2,4-dimethyl-5-thiazolyl C₂H₅ Ii.444 2,4-dimethyl-5-thiazolyl n-C₃H₇ Ii.445 2,4-dimethyl-5-thiazolyl i-C₃H₇ Ii.446 2,4-dimethyl-5-thiazolyl n-C₄H₉ Ii.447 2,4-dimethyl-5-thiazolyl CH₂—CH═CH₂ Ii.448 2,4-dimethyl-5-thiazolyl CH₂—C≡CH Ii.449 2,4-dimethyl-5-thiazolyl phenyl Ii.450 2,4-dimethyl-5-thiazolyl benzyl Ii.451 3-methyl-5-isothiazolyl CH₃ Ii.452 3-methyl-5-isothiazolyl C₂H₅ Ii.453 3-methyl-5-isothiazolyl n-C₃H₇ Ii.454 3-methyl-5-isothiazolyl i-C₃H₇ Ii.455 3-methyl-5-isothiazolyl n-C₄H₉ Ii.456 3-methyl-5-isothiazolyl CH₂—CH═CH₂ Ii.457 3-methyl-5-isothiazolyl CH₂—C≡CH Ii.458 3-methyl-5-isothiazolyl phenyl Ii.459 3-methyl-5-isothiazolyl benzyl Ii.460 1,3,5-trimethyl-4-pyrazolyl CH₃ Ii.461 1,3,5-trimethyl-4-pyrazolyl C₂H₅ Ii.462 1,3,5-trimethyl-4-pyrazolyl n-C₃H₇ Ii.463 1,3,5-trimethyl-4-pyrazolyl i-C₃H₇ Ii.464 1,3,5-trimethyl-4-pyrazolyl n-C₄H₉ Ii.465 1,3,5-trimethyl-4-pyrazolyl CH₂—CH═CH₂ Ii.466 1,3,5-trimethyl-4-pyrazolyl CH₂—C≡CH Ii.467 1,3,5-trimethyl-4-pyrazolyl phenyl Ii.468 1,3,5-trimethyl-4-pyrazolyl benzyl Ii.469 5-chloro-1,3-dimethyl-4-pyrazolyl CH₃ Ii.470 5-chloro-1,3-dimethyl-4-pyrazolyl C₂H₅ Ii.471 5-chloro-1,3-dimethyl-4-pyrazolyl n-C₃H₇ Ii.472 5-chloro-1,3-dimethyl-4-pyrazolyl i-C₃H₇ Ii.473 5-chloro-1,3-dimethyl-4-pyrazolyl n-C₄H₉ Ii.474 5-chloro-1,3-dimethyl-4-pyrazolyl CH₂—CH═CH₂ Ii.475 5-chloro-1,3-dimethyl-4-pyrazolyl CH₂—C≡CH Ii.476 5-chloro-1,3-dimethyl-4-pyrazolyl phenyl Ii.477 5-chloro-1,3-dimethyl-4-pyrazolyl benzyl Ii.478 1,4-dimethyl-3-pyrazolyl CH₃ Ii.479 1,4-dimethyl-3-pyrazolyl C₂H₅ Ii.480 1,4-dimethyl-3-pyrazolyl n-C₃H₇ Ii.481 1,4-dimethyl-3-pyrazolyl i-C₃H₇ Ii.482 1,4-dimethyl-3-pyrazolyl n-C₄H₉ Ii.483 1,4-dimethyl-3-pyrazolyl CH₂—CH═CH₂ Ii.484 1,4-dimethyl-3-pyrazolyl CH₂—C≡CH Ii.485 1,4-dimethyl-3-pyrazolyl phenyl Ii.486 1,4-dimethyl-3-pyrazolyl benzyl Ii.487 2-pyridyl CH₃ Ii.488 2-pyridyl C₂H₅ Ii.489 2-pyridyl n-C₃H₇ Ii.490 2-pyridyl i-C₃H₇ Ii.491 2-pyridyl n-C₄H₉ Ii.492 2-pyridyl CH₂—CH═CH₂ Ii.493 2-pyridyl CH₂—C≡CH Ii.494 2-pyridyl phenyl Ii.495 2-pyridyl benzyl Ii.496 3-pyridyl CH₃ Ii.497 3-pyridyl C₂H₅ Ii.498 3-pyridyl n-C₃H₇ Ii.499 3-pyridyl i-C₃H₇ Ii.500 3-pyridyl n-C₄H₉ Ii.501 3-pyridyl CH₂—CH═CH₂ Ii.502 3-pyridyl CH₂—C≡CH Ii.503 3-pyridyl phenyl Ii.504 3-pyridyl benzyl Ii.505 4-pyridyl CH₃ Ii.506 4-pyridyl C₂H₅ Ii.507 4-pyridyl n-C₃H₇ Ii.508 4-pyridyl i-C₃H₇ Ii.509 4-pyridyl n-C₄H₉ Ii.510 4-pyridyl CH₂—CH═CH₂ Ii.511 4-pyridyl CH₂—C≡CH Ii.512 4-pyridyl phenyl Ii.513 4-pyridyl benzyl Ii.514 2-chloro-3-pyridyl CH₃ Ii.515 2-chloro-3-pyridyl C₂H₅ Ii.516 2-chloro-3-pyridyl n-C₃H₇ Ii.517 2-chloro-3-pyridyl i-C₃H₇ Ii.518 2-chloro-3-pyridyl n-C₄H₉ Ii.519 2-chloro-3-pyridyl CH₂—CH═CH₂ Ii.520 2-chloro-3-pyridyl CH₂—C≡CH Ii.521 2-chloro-3-pyridyl phenyl Ii.522 2-chloro-3-pyridyl benzyl Ii.523 2-chloro-5-pyridyl CH₃ Ii.524 2-chloro-5-pyridyl C₂H₅ Ii.525 2-chloro-5-pyridyl n-C₃H₇ Ii.526 2-chloro-5-pyridyl i-C₃H₇ Ii.527 2-chloro-5-pyridyl n-C₄H₉ Ii.528 2-chloro-5-pyridyl CH₂—CH═CH₂ Ii.529 2-chloro-5-pyridyl CH₂—C≡CH Ii.530 2-chloro-5-pyridyl phenyl Ii.531 2-chloro-5-pyridyl benzyl Ii.532 2-chloro-4-pyridyl CH₃ Ii.533 2-chloro-4-pyridyl C₂H₅ Ii.534 2-chloro-4-pyridyl n-C₃H₇ Ii.535 2-chloro-4-pyridyl i-C₃H₇ Ii.536 2-chloro-4-pyridyl n-C₄H₉ Ii.537 2-chloro-4-pyridyl CH₂—CH═CH₂ Ii.538 2-chloro-4-pyridyl CH₂—C≡CH Ii.539 2-chloro-4-pyridyl phenyl Ii.540 2-chloro-4-pyridyl benzyl Ii.541 3-chloro-4-pyridyl CH₃ Ii.542 3-chloro-4-pyridyl C₂H₅ Ii.543 3-chloro-4-pyridyl n-C₃H₇ Ii.544 3-chloro-4-pyridyl i-C₃H₇ Ii.545 3-chloro-4-pyridyl n-C₄H₉ Ii.546 3-chloro-4-pyridyl CH₂—CH═CH₂ Ii.547 3-chloro-4-pyridyl CH₂—C≡CH Ii.548 3-chloro-4-pyridyl phenyl Ii.549 3-chloro-4-pyridyl benzyl Ii.550 2-methyl-3-pyridyl CH₃ Ii.551 2-methyl-3-pyridyl C₂H₅ Ii.552 2-methyl-3-pyridyl n-C₃H₇ Ii.553 2-methyl-3-pyridyl i-C₃H₇ Ii.554 2-methyl-3-pyridyl n-C₄H₉ Ii.555 2-methyl-3-pyridyl CH₂—CH═CH₂ Ii.556 2-methyl-3-pyridyl CH₂—C≡CH Ii.557 2-methyl-3-pyridyl phenyl Ii.558 2-methyl-3-pyridyl benzyl Ii.559 2-(methylthio)-3-pyridyl CH₃ Ii.560 2-(methylthio)-3-pyridyl C₂H₅ Ii.561 2-(methylthio)-3-pyridyl n-C₃H₇ Ii.562 2-(methylthio)-3-pyridyl i-C₃H₇ Ii.563 2-(methylthio)-3-pyridyl n-C₄H₉ Ii.564 2-(methylthio)-3-pyridyl CH₂—CH═CH₂ Ii.565 2-(methylthio)-3-pyridyl CH₂—C≡CH Ii.566 2-(methylthio)-3-pyridyl phenyl Ii.567 2-(methylthio)-3-pyridyl benzyl Ii.568 4-(trifluoromethyl)-3-pyridyl CH₃ Ii.569 4-(trifluoromethyl)-3-pyridyl C₂H₅ Ii.570 4-(trifluoromethyl)-3-pyridyl n-C₃H₇ Ii.571 4-(trifluoromethyl)-3-pyridyl i-C₃H₇ Ii.572 4-(trifluoromethyl)-3-pyridyl n-C₄H₉ Ii.573 4-(trifluoromethyl)-3-pyridyl CH₂—CH═CH₂ Ii.574 4-(trifluoromethyl)-3-pyridyl CH₂—C≡CH Ii.575 4-(trifluoromethyl)-3-pyridyl phenyl Ii.576 4-(trifluoromethyl)-3-pyridyl benzyl Ii.577 2,6-dichloro-3-pyridyl CH₃ Ii.578 2,6-dichloro-3-pyridyl C₂H₅ Ii.579 2,6-dichloro-3-pyridyl n-C₃H₇ Ii.580 2,6-dichloro-3-pyridyl i-C₃H₇ Ii.581 2,6-dichloro-3-pyridyl n-C₄H₉ Ii.582 2,6-dichloro-3-pyridyl CH₂—CH═CH₂ Ii.583 2,6-dichloro-3-pyridyl CH₂—C≡CH Ii.584 2,6-dichloro-3-pyridyl phenyl Ii.585 2,6-dichloro-3-pyridyl benzyl Ii.586 2,6-dichloro-4-pyridyl CH₃ Ii.587 2,6-dichloro-4-pyridyl C₂H₅ Ii.588 2,6-dichloro-4-pyridyl n-C₃H₇ Ii.589 2,6-dichloro-4-pyridyl i-C₃H₇ Ii.590 2,6-dichloro-4-pyridyl n-C₄H₉ Ii.591 2,6-dichloro-4-pyridyl CH₂—CH═CH₂ Ii.592 2,6-dichloro-4-pyridyl CH₂—C≡CH Ii.593 2,6-dichloro-4-pyridyl phenyl Ii.594 2,6-dichloro-4-pyridyl benzyl Ii.595 2-chloro-4-methyl-3-pyridyl CH₃ Ii.596 2-chloro-4-methyl-3-pyridyl C₂H₅ Ii.597 2-chloro-4-methyl-3-pyridyl n-C₃H₇ Ii.598 2-chloro-4-methyl-3-pyridyl i-C₃H₇ Ii.599 2-chloro-4-methyl-3-pyridyl n-C₄H₉ Ii.600 2-chloro-4-methyl-3-pyridyl CH₂—CH═CH₂ Ii.601 2-chloro-4-methyl-3-pyridyl CH₂—C≡CH Ii.602 2-chloro-4-methyl-3-pyridyl phenyl Ii.603 2-chloro-4-methyl-3-pyridyl benzyl

Finally, particular preference is given to the heterocyclic tetrazolinonecarboxamides below:

The compounds Ik.1-Ik.603 which differ from the corresponding compounds Ii.1-Ii.603 only in that Het is tetrahydrofuran-3-yl:

The compounds Il.1-Il.603 which differ from the corresponding compounds Ii.1-Ii.603 only in that Het is furan-3-yl:

The compounds Im.1-Im.603 which differ from the corresponding compounds Ii.1-Ii.603 only in that Het is 2,4-dimethylfuran-3-yl:

The compounds In.1-In.603 which differ from the corresponding compounds Ii.1-Ii.603 only in that Het is tetrahydro-2H-thio-pyran-4-yl:

The compounds Io.1-Io.603 which differ from the corresponding compounds Ii.1-Ii.603 only in that Het is tetrahydrothiophen-3-yl:

The compounds Ip.1-Ip.603 which differ from the corresponding compounds Ii.1-Ii.603 only in that Het is thiophen-3-yl:

The compounds Iq.1-Iq.603 which differ from the corresponding compounds Ii.1-Ii.603 only in that Het is 2,4-dimethylthiophen-3-yl:

Likewise, very particular preference is given to the substituted tetrazolinecarboxamides of the formula I where the variables have the following meaning:

Het is tetrahydrofuran-3-yl, tetrahydrothiophen-3-yl, 2,4-dimethyltetrahydrothiophen-3-yl, tetrahydro-2H-pyran-4-yl or tetrahydro-2H-thiopyran-4yl;

R¹ is C₁-C₆-haloalkyl or phenyl, which may be unsubstituted or may carry one to four substituents and is in particular unsubstituted or may carry one to two substituents, selected from the group consisting of halogen, C₁-C₄-alkyl or C₁-C₄ -haloalkyl;

R² is C₁-C₆-alkyl; in particular C₁-C₄-alkyl.

The substituted tetrazolinonecarboxamides of the formula I can be obtained in a variety of ways, in particular by one of the following processes:

A) Reaction of tetrazolinones of the formula II in the presence of a base with a carbamoyl chloride of the formula III, or initial deprotonation of the tetrazolinone of the formula II with a base and, if desired, isolation of the resulting salt of the formula IV and subsequent reaction with a carbamoyl chloride of the formula III.

where M⁺ in the formula IV is a cation derived from the base, for example triethylammonium, tetraethylammonium, Na⁺, K⁺ or Ca²⁺/2.

B) Reaction of a tetrazolinonecarbonyl chloride of the formula VI in the presence of a base with an amine of the formula V.

Suitable bases for the two processes A) and B) are amines, such as triethylamine, pyridine and 4-dimethylaminopyridine, tetraalkyl- or tetraarylammonium hydroxides, such as tetraethylammonium hydroxide, alkali metal carbonates, bicarbonates and hydrides, such as sodium carbonate, sodium bicarbonate or sodium hydride, alkali metal hydroxides or alkaline earth metal hydroxides, such as sodium hydroxide, potassium hydroxide or calcium hydroxide.

The salts of the formula IV which are readily isolated, for example as triethylammonium, tetraethylammonium, sodium, potassium or calcium salts, can be obtained by reaction of the the tetrazolinones of the formula II with a base.

The tetrazolinones of the formula II are known per se and can be obtained, for example, by reacting the corresponding aliphatic or aromatic isocyanates with azidotrimethylsilane or with aluminum azide prepared in situ. (Houben-Weyl, Vol. E8d, pages 692-693, Thieme-Verlag Stuttgart 1994).

The carbamoyl chlorides of the formula II where the radical Het has the meanings listed for the compounds of the formula I and R² has also the meanings listed for the compounds of the formula I, with the exception of hydrogen, are novel.

The carbamoyl chlorides of the formula III having the substituents Het and R² listed in Table 3 are suitable for preparing the particularly preferred substituted tetrazolinonecarboxamides.

TABLE 3 No. Het R² III.1 tetrahydrofuran-3-yl CH₃ III.2 tetrahydrofuran-3-yl C₂H₅ III.3 tetrahydrofuran-3-yl n-C₃H₇ III.4 tetrahydrofuran-3-yl i-C₃H₇ III.5 tetrahydrofuran-3-yl n-C₄H₉ III.6 tetrahydrofuran-3-yl CH₂—CH═CH₂ III.7 tetrahydrofuran-3-yl CH₂—C≡CH III.8 tetrahydrofuran-3-yl phenyl III.9 tetrahydrofuran-3-yl benzyl III.10 tetrahydro-2H-pyran-4-yl CH₃ III.11 tetrahydro-2H-pyran-4-yl C₂H₅ III.12 tetrahydro-2H-pyran-4-yl n-C₃H₇ III.13 tetrahydro-2H-pyran-4-yl i-C₃H₇ III.14 tetrahydro-2H-pyran-4-yl n-C₄H₉ III.15 tetrahydro-2H-pyran-4-yl CH₂—CH═CH₂ III.16 tetrahydro-2H-pyran-4-yl CH₂—C≡CH III.17 tetrahydro-2H-pyran-4-yl phenyl III.18 tetrahydro-2H-pyran-4-yl benzyl III.19 tetrahydrothiophen-3-yl CH₃ III.20 tetrahydrothiophen-3-yl C₂H₅ III.21 tetrahydrothiophen-3-yl n-C₃H₇ III.22 tetrahydrothiophen-3-yl i-C₃H₇ III.23 tetrahydrothiophen-3-yl n-C₄H₉ III.24 tetrahydrothiophen-3-yl CH₂—CH═CH₂ III.25 tetrahydrothiophen-3-yl CH₂—C≡CH III.26 tetrahydrothiophen-3-yl phenyl III.27 tetrahydrothiophen-3-yl benzyl III.28 tetrahydro-2H-thiopyran-4-yl CH₃ III.29 tetrahydro-2H-thiopyran-4-yl C₂H₅ III.30 tetrahydro-2H-thiopyran-4-yl n-C₃H₇ III.31 tetrahydro-2H-thiopyran-4-yl i-C₃H₇ III.32 tetrahydro-2H-thiopyran-4-yl n-C₄H₉ III.33 tetrahydro-2H-thiopyran-4-yl CH₂—CH═CH₂ III.34 tetrahydro-2H-thiopyran-4-yl CH₂—C≡CH III.35 tetrahydro-2H-thiopyran-4-yl phenyl III.36 tetrahydro-2H-thiopyran-4-yl benzyl III.37 furan-3-yl CH₃ III.38 furan-3-yl C₂H₅ III.39 furan-3-yl n-C₃H₇ III.40 furan-3-yl i-C₃H₇ III.41 furan-3-yl n-C₄H₉ III.42 furan-3-yl CH₂—CH═CH₂ III.43 furan-3-yl CH₂—C≡CH III.44 furan-3-yl phenyl III.45 furan-3-yl benzyl III.46 2,4-dimethylfuran-3-yl CH₃ III.47 2,4-dimethylfuran-3-yl C₂H₅ III.48 2,4-dimethylfuran-3-yl n-C₃H₇ III.49 2,4-dimethylfuran-3-yl i-C₃H₇ III.50 2,4-dimethylfuran-3-yl n-C₄H₉ III.51 2,4-dimethylfuran-3-yl CH₂—CH═CH₂ III.52 2,4-dimethylfuran-3-yl CH₂—C≡CH III.53 2,4-dimethylfuran-3-yl phenyl III.54 2,4-dimethylfuran-3-yl benzyl III.55 thiophen-3-yl CH₃ III.56 thiophen-3-yl C₂H₅ III.57 thiophen-3-yl n-C₃H₇ III.58 thiophen-3-yl i-C₃H₇ III.59 thiophen-3-yl n-C₄H₉ III.60 thiophen-3-yl CH₂—CH═CH₂ III.61 thiophen-3-yl CH₂—C≡CH III.62 thiophen-3-yl phenyl III.63 thiophen-3-yl benzyl III.64 2,4-dimethylthiophen-3-yl CH₃ III.65 2,4-dimethylthiophen-3-yl C₂H₅ III.66 2,4-dimethylthiophen-3-yl n-C₃H₇ III.67 2,4-dimethylthiophen-3-yl i-C₃H₇ III.68 2,4-dimethylthiophen-3-yl n-C₄H₉ III.69 2,4-dimethylthiophen-3-yl CH₂—CH═CH₂ III.70 2,4-dimethylthiophen-3-yl CH₂—C≡CH III.71 2,4-dimethylthiophen-3-yl phenyl III.72 2,4-dimethylthiophen-3-yl benzyl

The particularly preferred embodiments of the carbamoyl chlorides of the formula III with respect to the variables R² and Het correspond to those of the substituted tetrazolinonecarboxamides of the formula I.

The carbamoyl chlorides of the formula III can be prepared, for example, by phosgenation of the corresponding amines of the formula V. Suitable phosgenating agents are phosgene, diphosgene or triphosgene. The phosgenation can alternatively be carried out in the presence or the absence of a base, for example one of the bases mentioned above. It is also possible to convert the amine of the formula V prior to phosgenation by reaction with an acid into the corresponding acid addition salt, for example into the hydrochlorides using hydrogen chloride.

A process suitable for preparing the amines of the formula V is, for example, the reductive amination of heterocyclic ketones of the formula VII with amines of the formula VIII, or, alternatively, the reductive amination of heterocyclic amines of the formula IX with aldehydes or ketones of the formula X. This reaction is well known per se (for example A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, J. Org. Chem. 61 (1996), 3849, and the literature cited therein).

where

n,m is the integer 1 or 2;

q is the integer 0, 1 or 2;

Y is O or S;

Z is F, Cl, Br, I, C₁-C₆-alkyl or C₁-C₆-haloalkyl;

R^(a), R^(b) R^(a) and R^(b) together with the CH group to which they are attached form the radical R² which is, as far as possible, as defined for the compounds of the formula I.

Furthermore, the amines of the formula V can also be prepared by acylation of amines of the formula IX and subsequent reduction of the amides XI, which are formed as intermediate. Both reactions are known per se (see, for example, Houbey-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag, Vol. E5, Stuttgart 1985, p. 972 ff., p. 977 ff. and Vol. XI/1, Stuttgart 1957, p. 574 ff.).

where —CH₂R^(c) is a radical R², as defined for the compounds of the formula I.

Furthermore, amines of the formula V where Het=thiophen-3-yl or furan-3-yl with or without substitution can be prepared by reaction of compounds of formula XII, which may for their part be present as tautomers XIIa or XIIb or mixtures thereof, with amines R²—NH₂, if desired in the presence of a catalyst, for example acids, such as hydrochloric acid or sulfuric acid or Lewis acids, such as boron trifluoride, zinc chloride or titanium tetrachloride,

where

p is 0, 1, 2 or 3;

Q is oxygen or sulfur;

R^(d) is halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl.

The tetrazolinonecarbonyl chlorides of the formula VI which are employed for preparing the substituted tetrazolinonecarboxamides of the formula I according to the invention by process B) can be obtained by phosgenation of the corresponding tetrazolinones of the formula II, as described, for example, in EP-A 764 642.

The reactions to prepare the substituted tetrazolinonecarboxamides of the formula I according to the invention and the intermediates of the formulae II to XII required for their preparation are generally carried out in an inert organic solvent, for example in aliphatic or aromatic hydrocarbons, such as hexane, cyclohexane and toluene, halogenated hydrocarbons, such as dichloromethane or 1,2-dichloroethane, ethers, such as diethyl ether, tetrahydrofuran or dioxane, or in aprotic solvents, such as dimethylformamide, dimethyl sulfoxide and acetonitrile, or else in mixtures of the abovementioned solvents.

For all reactions mentioned, the reaction temperature is between the melting point and the boiling point of the reaction mixture, preferably (unless stated otherwise) between 0 and 100° C. To obtain high conversions, it may be advantageous to carry out the reaction at the boiling point of the reaction mixture. The reaction partners are generally employed in equimolar amounts. However, to obtain a better yield, it may also be advantageous to employ one or more reaction partners in an excess of up to approximately ten times the molar amount. The abovementioned reactions are advantageously carried out under atmospheric pressure or under the inherent pressure of the reaction mixture in question.

The substituted tetrazolinonecarboxamides I can normally be prepared by one of the synthesis methods mentioned above. However, for reasons of economy or process engineering, it may be more expedient to prepare some compounds I from similar tetrazolinonecarboxamides which, however, differ in particular in the meaning of the radical R¹ or R², the preparation being carried out in a manner known per se, e.g. by alkylation, condensation reaction, oxidation, olefination, reduction, etherification, esterification or Wittig reaction.

Those starting compounds for the individual processes which are not already known can be obtained in a manner known per se or by a method similar to one of the processes described.

The reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water followed by isolation of the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, partitioning the residue in a mixture of water and a suitable organic solvent and working up the organic phase to give the product.

The substituted tetrazolinonecarboxamides I may be obtained from the preparation in the form of isomer mixtures, but, if desired, the latter can be separated into the essentially pure isomers by the methods conventionally used for this purpose, such as crystallization or chromatography, also on an optically active adsorbate. Pure optically active isomers may be prepared advantageously from corresponding optically active starting materials.

The compounds I, both as isomer mixtures and in the form of the pure isomers, are suitable as herbicides. The herbicidal compositions comprising I effect very good control of vegetation on non-crop areas, especially at high rates of application. In crops such as wheat, rice, maize, soybeans and cotton, they act against broad-leaved weeds and grass weeds without damaging the crop plants substantially. This effect is observed especially at low rates of application.

Depending on the application method in question, the compounds I, or the herbicidal compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Suitable crops are, for example, the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I can also be used in crops which tolerate the action of herbicides due to breeding, including genetic engineering methods.

The herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less well tolerated by certain crop plants, it is possible to use application techniques in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into as little contact as possible, if any, with the leaves of the sensitive crop plants while reaching the leaves of undesirable plants which grow underneath, or the bare soil surface (post-directed, lay-by).

The compounds I, or the herbicidal compositions comprising them, can be applied, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend on the intended purposes; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.

Suitable inert auxiliaries are essentially: Mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds I, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates from active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, and these concentrates are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, of alkyl- and alkylarylsulfonates, of alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing or concomitant grinding of the active substances with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active ingredients I in the ready-to-use products can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The formulation examples which follow illustrate the preparation of the compounds according to the invention:

I. 20 parts by weight of the compound No. Ia.20 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

II. 20 parts by weight of the compound No. Ia.29 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

III. 20 parts by weight of the active ingredient No. Ia.155 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

IV. 20 parts by weight of the active ingredient No. Ia.227 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-a-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.

V. 3 parts by weight of the active ingredient No. Ie.19 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active ingredient.

VI. 20 parts by weight of the active ingredient No. Ie.28 are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglylcol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the active ingredient No. Ia.226 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the active ingredient No. Ia.20 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil; BASF AG). This gives a stable emulsion concentrate.

To widen the spectrum of action and to achieve synergistic effects, the substituted tetrazolinonecarboxamides may be mixed, and applied jointly, with a large number of representatives of other groups of herbicidally or growth-regulating active ingredients. Suitable examples of components in mixtures are 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetaryl/aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxirans, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

Moreover, it may be advantageous to apply the compounds I, alone or in combination with other herbicides, in the form of a mixture with even further crop protection agents, for example with pesticides or agents for controlling phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

Depending on the intended aim, the season, the target plant and the growth stage, the rates of application of active ingredient I are from 0.001 to 3.0, preferably 0.01 to 1.0, kg of active substance (a.s.)/ha.

PREPARATION EXAMPLES Example 1 N-ethyl-N-(tetrahydro-2H-pyran-4-yl)-4-(2-chlorophenyl)-4,5-dihydro-1H-tetrazol-5-one-1-carboxamide (No. Ia.20)

3.7 g (19 mmol) of 1-(2-chlorophenyl)-1,2-dihydro-5H-tetrazol-5-one, 3.6 g (19 mmol) of N-ethyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride and 2.6 g (21 mmol) of 4-dimethylaminopyridine in 150 ml of toluene were heated under reflux for 5 hours. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (eluent hexane/ethyl acetate 2:1). Yield 5.5 g. ¹H NMR (270 MHz, in CDCl₃): δ=1.20-1.40 (m, 3H), 1.80-2.05 (m, 4H), 3.30-3.60 (m, 4H), 3.70-4.50 (m, 3H), 7.40-7.60 (m, 4H).

Intermediate 1.1

Ethyl(tetrahydro-2H-pyran-4-yl)amine

At 0° C. and with efficient cooling, 51 g (0.5 mol) of conc. sulfuric acid were added dropwise to a solution of 105 g (2.3 mol) of ethylamine in 0.5 l of methanol. 50 g (0.5 mol) of tetrahydro-2H-pyran-4-one and 18.8 g (0.3 mol) of sodium cyanoborhydride were then added successively. After 16 hours at room temperature, the methanol was distilled off, an excess of 10% strength aqueous sodium hydroxide solution was added and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were washed neutral with water, dried over magnesium sulfate and filtered and the residue was distilled. Bp. 76-82° C. (20 mbar), yield 24 g. ¹H NMR (250 MHz, in CDCl₃): δ=0.86 (s, 1H), 1.13 (t, 3H), 1.40 (dq, 2H), 1.84 (m, 2H), 2.68 (m, 3H), 3.40 (dt, 2H), 3.98 (m, 2H).

Intermediate 1.2

N-ethyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride (No. III.11)

At −30° C., a solution of 19 g (0.15 mol) of ethyl(tetrahydro-2H-pyran-4-yl)amine and 14.8 g (0.15 mol) of triethylamine in 10 ml of dichloromethane was slowly added dropwise to a solution of 44 g (0.44 mol) of phosgene in 100 ml of dichloromethane. The mixture was slowly warmed to room temperature (over a period of approximately 3 hours) and then heated under reflux for 30 minutes, excess phosgene was removed using a nitrogen stream, and the solution was concentrated. 200 ml of hexane were added, the solids were filtered off and the filtrate was concentrated. Yield 25.3 g. MS (m/z): 192 [M+H]⁺, 156 [M−Cl]⁺.

Example 2 N-methyl-N-(tetrahydro-2H-thiopyran-4-yl)-4-(2-bromophenyl)-4,5-dihydro-1H-tetrazol-5-one-1-carboxamide (No. Ie.28)

Similarly to the process described in Example 1, 2.5 g (10 mmol) of 1-(2-bromophenyl)-1,2-dihydro-5H-tetrazol-5-one, 2 g (10 mmol) of N-methyl-N-(tetrahydro-2H-thiopyran-4-yl)carbamoyl chloride and 1.5 g (12 mmol) of 4-dimethylaminopyridine were reacted. Yield 2.5 g.

Intermediate 2.1

Methyl(tetrahydro-2H-thiopyran-4-yl)amine

Similarly to the process described in intermediate 1.1, 36.8 g (1.2 mol) of methylamine, 30 g (0.26 mol) of tetrahydro-2H-thiopyran-4-one and 9.7 g (0.15 mol) of sodium cyanoborhydride were reacted. Bp. 98° C. (25 mbar), yield 10 g.

¹H NMR (400 MHz, in CDCl₃): δ=1.06 (s, 1H), 1.48 (dq, 2H), 2.16 (m, 2H), 2.35 (tt, 1H), 2.42 (s, 3H), 2.60-2.70 (m, 4H).

Intermediate 2.2

N-Methyl-N-(tetrahydro-2H-thiopyran-4-yl)carbamoyl chloride (No. III.28)

Similarly to the method described in intermediate 1.2, 22.8 g (0.23 mol) of phosgene, 10 g (76 mmol) of methyl(tetrahydro-2H-thiopyran-4-yl)amine and 7.8 g (76 mmol) of triethylamine were reacted. Yield 13.4 g. MS (m/z): 193 [M]⁺, 158 [M−Cl]⁺.

Example 3 N-(2,4-Dimethylthiophen-3-yl)-N-n-propyl-4,5-dihydro-4-(2-fluoro-phenyl)-1H-tetrazol-5-one-1-carboxamide (No. Ih.12)

1.17 g (6.5 mmol) of 1,2-dihydro-1-(2-fluorophenyl)-5H-tetrazol-5-one, 1.5 g (6.5 mmol) of N-(2,4-dimethyl-thiophen-3-yl)-N-n-propylcarbamoyl chloride and 1.19 g (9.7 mmol) of 4-dimethylaminopyridine were reacted by the method of the process described in Example 1. Yield 1.9 g.

Precursor 3.1

2,4-Dimethylthiophen-3-yl-(n-propyl)amine

In an atmosphere of inert gas, 34.6 g (0.59 mol) of propylamine were admixed with 10.6 g (78 mmol) of anhydrous zinc chloride powder in the course of which the temperature of the mixture rose strongly. The solution was then admixed with 50 g (0.39 mol) of 2,4-dimethyl-3-hydroxythiophene, introduced into an autoclave and heated at 1700° C. under pressure (approximately 5 bar) for 16 hours. After cooling, the mixture was made alkaline using 50 ml of 33% strength aqueous sodium hydroxide solution and extracted twice with hexane, the combined organic phases were washed three times with water, dried over magnesium sulfate, filtered and concentrated under water pump vacuum, and the residue was distilled. Yield 31.2 g (47%), b.p. 88° C. (2 mbar). ¹H NMR (270 MHz in CDCl₃):δ=0.96 (t, 3H), 1.56 (sext., 2H), 2.12 (s, 3H), 2.31 (s, 3H), 2.96 (t, 2H), 3.18 (s, 1H), 6.61 (s, 1H).

Intermediate 3.2

N-(2,4-Dimethylthiophen-3-yl)-N-n-propylcarbamoyl chloride (No. III.66)

54.5 g (0.54 mol) of phosgene, 31 g (0.18 mol) of 2,4-dimethylthiophen-3-yl-(n-propyl)amine and 18.5 g (0.18 mol) of triethylamine were reacted similarly to the process described in Intermediate 1.2. Yield 40 g. MS (m/z): 231 [M]⁺, 202 [M−C₂H₅]⁺, 196 [M−Cl]⁺.

Example 4

N-Methyl-N-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-4-(2-trifluoro-methylphenyl)-5H-tetrazol-5-one-1-carboxamide (No. Ia.388)

1.94 g (8,45 mmol) of 1,2-dihydro-1-(2-trifluoromethylphenyl)-5H-tetrazol-5-one, 1.5 g (8.5 mmol) of N-methyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride and 1.55 g (12.7 mmol) of 4-dimethylaminopyridine were reacted by the method of the process described in Example 1. Yield 0.55 g.

Intermediate 4.1

N-Methyl-N-(tetrahydro-2H-pyran-4-yl)amine

At −70° C., 170 g (5.5 mol) of gaseous methylamine were introduced into 1.5 l of methanol. The solution was admixed dropwise with 100 g (1 mol) of sulfuric acid. 100 g (1 mol) of tetrahydro-4H-pyran-4-one and 36.4 g (0.6 mol) of sodium borocyanohydride were added in succession, and the mixture was stirred at room temperature for 3 days, resulting in a white precipitate. The solution was filtered and the filtrate was distilled. B.p. 56-58° C. (12 mm), yield 96 g. ¹H NMR (270 MHz, in CDCl₃): δ=1.30 (s, 1H), 1.38 (dq, 2H), 1.85 (dd, 2H), 2.43 (s, 3H), 2.57 (tt, 1H), 3.41 (dt, 2H), 3.99 (dt, 2H).

Intermediate 4.2

N-Methyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride (No. III.10)

248 g (2.5 mol) of phosgene, 96 g (0.83 mol) of N-methyl-N-(tetrahydro-2H-pyran-4-yl)amine and 84 g (0.83 mol) of triethylamine were reacted by the method of the process described in Intermediate 1.2. Yield 108 g. ¹H NMR (250 MHz, in CDCl₃): δ=1.60-1.95 (m, 4H), 2.94 and 3.01 (2 s, together 3H), 3.35-3.55 (rm, 2H), 3.95-4.10 (m, 2H), 4.27-4.46 (m, 1H).

Example 5 N-Propyl-N-(tetrahydrofuran-3-yl)-4,5-dihydro-4-(2-fluorophenyl)-1H-tetrazol-5-one-1-carboxamide (No. Ib.12)

1.4 g (7.8 mmol) of 1,2-dihydro-1-(2-fluorophenyl)-5H-tetrazol-5-one, 1.5 g (7.8 mmol) of N-propyl-N-(tetrahydro-furan-3-yl)carbamoyl chloride and 1.29 g (10 mmol) of 4-dimethylaminopyridine were reacted by the method of the process described in Example 1. Yield 2.1 g.

Intermediate 5.1

N-(Tetrahydrofuran-3-yl)propionamide

A solution of 50 g of 3-aminotetrahydrofuran in 200 ml of dichloromethane was mixed with 63.8 g (0.63 mol) of triethylamine. 58.4 g (0.63 mol) of propionyl chloride were added dropwise with ice-cooling. The mixture was stirred at room temperature for 2 days, resulting in a white precipitate. The solution was filtered and the filtrate was distilled. B.p. 145° C. (12 mm), yield 81 g. ¹H NMR (270 MHz, in CDCl₃): δ=1.14 (t, 3 H), 1.83 (m, 1H), 2.22 (q, 2H), 2.31 (m, 1H), 3.64 (dd, 1H), 3.72-3.98 (m, 3H), 4.50 (m, 1H), 6.57 (s, 1H).

Intermediate 5.2

N-Propyl-N-(tetrahydrofuran-3-yl)amine

A suspension of 21.7 g (0.57 mol) of lithium aluminum hydride in 500 ml of THF was admixed dropwise with a solution of 81 g (0.57 mol) of N-(tetrahydrofuran-3-yl)propionamide, and the solution was heated at reflux for 2 h. Excess lithium aluminum hydride was hydrolyzed by dropwise addition of 16 ml of water, 50 ml of 10% strength aqueous sodium hydroxide solution and another 45 ml of water. The white suspension was heated at reflux for one hour, causing the insoluble components to aggregate to a coarse white precipitate. The mixture was filtered off from the precipitate, the precipitate was thoroughly rinsed with ether and the combined filtrates were distilled. B.p. 64° C. (12 mm), yield 41 g. ¹H NMR (270 MHz, in CDCl₃): δ=0.92 (t, 3H), 1.15 (s, 1H), 1.50 (sext., 2H), 1.70 (m, 1H), 2.10 (m, 1H), 2.55 (m, 2H), 3.38 (m, 1H), 3.56 (dd, 1H), 3.70-3.96 (m, 3H).

Intermediate 5.3

N-Propyl-N-(tetrahydrofuran-3-yl)carbamoyl chloride (No. III.3)

94 g (0.95 mol) of phosgene, 41 g (0.32 mol) of N-propyl-N-(tetrahydrofuran-3-yl)amine and 32 g (0.32 mol) of triethylamine were reacted by the method of the process described in Intermediate 1.2. Yield 54 g. ¹H NMR (270 MHz, in CDCl₃): δ=0.92 (t, 3H), 1.70 (sext., 2H), 2.02 (s, 1H), 2.30 (s, 1H), 3.20-3.40 (m, 2H), 3.65-3.85 (m, 3H), 4.05 (m, 1H), 4.50-4.70 and 4.85-5.05 (2 m, together 1H).

The intermediates of the formula V mentioned below were prepared by the methods of the processes described in Intermediates 1.1, 2.1 and 4.1.

n-Propyl(tetrahydro-2H-pyran-4-yl)amine: B.p. 90° C. (12 mm). ¹H NMR (270 MHz, in CDCl₃): δ=0.93 (t, 3H), 1.30-1.60 (m, 5H), 1.83 (dd, 2H), 2.63 (t, 2H), 2.68 (tt, 1H), 3.40 (dt, 2H), 3.99 (dt, 2H).

i-Propyl(tetrahydro-2H-pyran-4-yl)amine: B.p. 104° C. ¹H NMR (360 MHz, in CDCl₃): δ=0.72 (s, 1H), 1.07 (d, 6H), 1.36 (dq, 2H), 1.84 (d, 2H), 2.75 (tt, 1H), 3.00 (sept., 1H), 3.41 (t, 2H), 3.97 (d, 2H).

n-Propyl(tetrahydrothiophen-3-yl)amine: B.p. 104-108° C. (12 mm). ¹H NMR (270 MHz, in CDCl₃): δ=0.94 (t, 3H), 1.26 (s, 1H), 1.51 (sext., 2H), 1.83-2.10 (m, 2H), 2.55-2.70 (m, 3H), 2.87 (t, 2H), 2.96 (dd, 1H), 3.44 (quint., 1H).

Ethyl(tetrahydro-2H-thiopyran-4-yl)amine: B.p. 100° C. (12 mm). ¹H NMR (270 MHz, in CDCl₃): δ=0.96 (s, 1H), 1.11 (t, 3H), 1.40-1.60 (m, 2H), 2.17 (dq, 2H), 2.47 (tt, 1H), 2.60-2.75 (m, 6H).

n-Propyl(tetrahydro-2H-thiopyran-4-yl)amine: B.p. 115° C. (12 mm). ¹H NMR (270 MHz, in CDCl₃): δ=0.93 (t, 3H), 1.05 (s, 1H), 1.40-1.60 (m, 4H), 2.18 (dq, 2H), 2.45 (tt, 1H), 2.60 (t, 2H), 2.62-2.75 (m, 4H).

The intermediates of the formula III mentioned below were prepared by the methods of the processes described in Intermediates 1.2, 2.2, 3.2, 4.2 and 5.3.

N-n-Propyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride (No. III. 12): ¹H NMR (270 MHz, in CDCl₃): δ=0.93 (t, 3H), 1.55-2.00 (m, 6H), 3.15-3.50 (m, 4H), 3.95-4.10 (m, 2H), 4.10-4.40 (m, 1H).

N-i-Propyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride (No. III. 13): ¹H NMR (270 MHz, in CDCl₃): δ=1.24 (d, 3H), 1.38 (d, 3H), 1.65-1.95 (m, 4H), 3.30-3.50 (m, 2H), 3.62 (sept., 1H), 3.98-4.12 (m, 2H), 4.25-4.47 (m, 1H).

N-n-Propyl-N-(tetrahydrothiophen-3-yl)carbamoyl chloride (No. III.21): ¹H NMR (250 MHz, in CDCl₃): δ=0.92 (t, 3H), 1.50-1.70 (m, 2H), 2.16 (q, 2H), 2.85-3.05 (m, 2H), 3.47-3.75 (m, 4H), 4.00-4.10 (m, 1H).

N-Ethyl-N-(tetrahydro-2H-thiopyran-4-yl)carbamoyl chloride (No. III.29): ¹H NMR (250 MHz, in CDCl₃): δ=1.15-1.30 (m, 3H), 1.80-2.20 (m, 4H), 2.60-2.86 (m, 4H), 3.30-3.50 (m, 2H), 3.90-4.20 (m, 1H).

N-n-Propyl-N-(tetrahydro-2H-thiopyran-4-yl)carbamoyl chloride (No. III.30): ¹H NMR (270 MHz, in CDCl₃): δ=0.91 (t, 3H), 1.55-2.20 (m, 6H), 2.60-2.90 (m, 4H), 3.15-3.35 (m, 2H), 3.85-4.15 (m, 1H).

In the Tables 4 and 5 below, the physical data of the compounds of the formula I listed above are compiled, and compounds of the formula I are listed which were prepared in a similar manner:

TABLE 4 I

¹H NMR [ppm]/ No. X_(n) R² Het MS [m/z] Ia.1 H CH₃ tetrahydro-2H- 1.75-2.00(m, 4H), pyran-4-yl 3.04(s, 3H), 3.30-3.60(m, 2H), 3.70-3.95 and 4.35-4.55(2H, together 1H), 3.97-4.15 (m, 2H), 7.35-7.55 (m, 3H), 7.91(d, 2H) Ia.2 H C₂H₅ tetrahydro-2H- 1.20-1.40(m, 3H), pyran-4-yl 1.80-2.10(m, 4H), 3.30-3.60(m, 4H), 3.70-4.40(m, 3H), 7.35-7.58(m, 3H), 7.92(d, 2H) Ia.3 H n-C₃H₇ tetrahydro-2H- 0.80-1.05(m, 3H), pyran-4-yl 1.55-2.10(m, 6H), 3.25-3.55(m, 4H), 3.70-4.40(m, 3H), 7.35-7.58(m, 3H), 7.93(d, 2H) Ia.4 H i-C₃H₇ tetrahydro-2H- 1.45(d, 6H), 1.65-2.40 pyran-4-yl (m, 4H), 3.40(t, 2H), 3.50-3.70(m, 1H), 3.72-3.95(m, 1H), 4.00-4.10(m, 2H), 7.41(t, 1H), 7.51 (t, 2H), 7.91(d, 2H) Ia.10 2-F CH₃ tetrahydro-2H- 1.80-2.00(m, 4H), pyran-4-yl 3.05(s, 3H), 3.35-3.60(m, 2H), 3.75-3.90 and 4.40-4.55(2m, together, 1H), 4.00-4.15(m, 2H), 7.28-7.38(m, 2H), 7.50-7.60(m, 2H) Ia.11 2-F C₂H₅ tetrahydro-2H- 1.20-1.40(m, 3H), pyran-4-yl 1.80-2.10(m, 4H), 3.30-3.60(m, 4H), 3.70-4.40(m, 3H), 7.20-7.40(m, 2H), 7.45-7.60(m, 2H) Ia.12 2-F n-C₃H₇ tetrahydro-2H- 0.80-1.03(m, 3H), pyran-4-yl 1.55-2.05(m, 6H), 3.30-3.55(m, 4H), 3.70-4.40(m, 3H), 7.25-7.38(m, 2H), 7.47-7.62(m, 2H) Ia.13 2-F i-C₃H₇ tetrahydro-2H- 1.46(d, 6H), 1.65-2.30 pyran-4-yl (m, 4H), 3.41(t, 2H), 3.50-3.70(m, 1H), 3.71-3.96(m, 1H), 4.00-4.13(m, 2H), 7.25-7.38(m, 2H), 7.46-7.60(m, 2H), Ia.19 2-Cl CH₃ tetrahydro-2H- 1.75-2.05(m, 4H), pyran-4-yl 3.06(s, 3H), 3.30-3.60(m, 2H), 3.70-3.90 and 4.40-4.68(2m, together, 1H), 4.00-4.15(m, 2H), 7.40-7.65(m, 4H) Ia.20 2-Cl C₂H₅ tetrahydro-2H- 352 [M+H]⁺ pyran-4-yl Ia.21 2-Cl n-C₃H₇ tetrahydro-2H- 0.80-1.00(m, 3H), pyran-4-yl 1.55-2.05(m, 6H), 3.25-3.55(m, 4H), 3.70-4.45(m, 3H), 7.40-7.65(m, 4H) Ia.22 2-Cl i-C₃H₇ tetrahydro-2H- 1.47(d, 6H), 1.60-2.30 pyran-4-yl (m, 4H), 3.39(t, 2H), 3.50-3.70(m, 1H), 3.70-3.95(m, 1H), 4.00-4.13(m, 2H), 7.42-7.66(m, 4H) Ia.28 2-Br CH₃ tetrahydro-2H- 1.80-2.00(m, 4H), pyran-4-yl 3.05(s, 3H), 3.30-3.60(m, 2H), 3.75-3.90 and 4.40-4.55(2m, together 1H), 4.00-4.15(m, 2H), 7.40-7.55(m, 3H), 7.78(d, 1H) Ia.29 2-Br C₂H₅ tetrahydro-2H- 1.20-1.40(m, 3H), pyran-4-yl 1.80-2.10(m, 4H), 3.30-3.60(m, 4H), 3.70-4.50(m, 3H), 7.40-7.55(m, 3H), 7.79(d, 1H) Ia.30 2-Br n-C₃H₇ tetrahydro-2H- 0.80-1.05(m, 3H), pyran-4-yl 1.60-2.10(m, 6H), 3.30-3.55(m, 4H), 3.75-4.45(m, 3H), 7.40-7.55(m, 3H), 7.78(d, 1H) Ia.31 2-Br i-C₃H₇ tetrahydro-2H- 1.47(d, 6H), 1.65-2.40 pyran-4-yl (m, 4H), 3.39(t, 2H), 3.50-3.70(m, 1H), 3.72-3.95(m, 1H), 4.00-4.12(m, 2H), 7.38-7.55(m, 3H), 7.78(d, 1H) Ia.37 2-CH₃ CH₃ tetrahydro-2H- 1.75-2.00(m, 4H), pyran-4-yl 2.31(s, 3H), 3.04 (s, 3H), 3.30-3.60 (m, 2H), 3.70-3.90 and 4.40-4.55(2m, together 1H), 4.00-4.12(m, 2H), 7.30-7.47(m, 4H) Ia.38 2-CH₃ C₂H₅ tetrahydro-2H- 1.20-1.40(m, 3H), pyran-4-yl 1.80-2.10(m, 4H), 2.31(s, 3H), 3.30-3.55(m, 4H), 3.75-4.45(m, 3H), 7.30-7.46(m, 4H) Ia.39 2-CH₃ C₃H₇ tetrahydro-2H- 0.80-1.00(m, 3H), pyran-4-yl 1.55-2.05(m, 6H), 2.31(s, 3H), 3.30-3.60(m, 4H), 3.73-4.45(m, 3H), 7.30-7.48(m, 4H) Ia.40 2-CH₃ i-C₃H₇ tetrahydro-2H- 1.46(d, 6H), pyran-4-yl 1.70-2.40(m, 4H), 2.32(s, 3H), 3.39 (t, 2H), 3.50-3.70 (m, 1H), 3.72-3.95 (m, 1H), 4.00-4.10 (m, 2H), 7.30-7.45 (m, 4H) Ia.155 2,6-Cl₂ C₂H₅ tetrahydro-2H- 1.20-1.40(m, 3H), pyran-4-yl 1.80-2.00(m, 4H), 3.25-3.60(m, 4H), 3.70-4.50(m, 3H), 7.45-7.55(m, 3H) Ia.156 2,6-Cl₂ n-C₃H₇ tetrahydro-2H- 0.80-1.05(m, 3H), pyran-4-yl 1.50-2.05(m, 6H), 3.25-3.55(m, 4H), 3.70-4.50(m, 3H), 7.43-7.57(m, 3H) Ia.157 2,6-Cl₂ i-C₃H₇ tetrahydro-2H- 1.47(d, 6H), 1.65-2.40 pyran-4-yl (m, 4H), 3.36(t, 2H), 3.50-3.67(m, 1H), 3.70-3.90(m, 1H), 4.00-4.12(m, 2H), 7.25-7.45(m, 3H) Ia.199 2-Cl, CH₃ tetrahydro-2H- 1.70-2.00(m, 4H), 6-CH₃ pyran-4-yl 2.28(s, 3H), 3.02(s, 3H), 3.25-3.60(m, 2H), 3.70-3.85 and 4.35-4.55(2m, together 1H), 3.95-4.15(m, 2H), 7.24-7.44(m, 3H) Ia.200 2-Cl, C₂H₅ tetrahydro-2H- 1.20-1.40(m, 3H), 6-CH₃ pyran-4-yl 1.75-2.00(m, 4H), 2.29(s, 3H), 3.30-3.60(m, 4H), 3.65-4.50(m, 3H), 7.22-7.45(m, 3H) Ia.201 2-Cl, n-C₃H₇ tetrahydro-2H- 0.80-1.05(m, 3H), 6-CH₃ pyran-4-yl 1.55-2.05(m, 6H), 2.29(s, 3H), 3.25-3.60(m, 4H), 3.70-4.50(m, 3H), 7.28-7.45(m, 3H) Ia.202 2-Cl, i-C₃H₇ tetrahydro-2H- 1.48(s, 6H), 1.70-2.30 6-Cl₃ pyran-4-yl (m, 4H), 2.29(s, 3H), 3.30-3.45(m, 2H), 3.50-3.67(m, 1H), 3.70-3.90(m, 1H), 4.00-4.12(m, 2H), 7.25-7.45(m, 3H) Ia.226 3-Cl, CH₃ tetrahydro-2H- 1.28(d, 6H), 1.78-2.04 4-i-C₃H₇ pyran-4-yl (m, 4H), 3.04(s, 3H), 3.33-3.60(m, 2H), 3.44(sept., 1H) 3.70-4.55(m, 3H), 7.43(d, 1H), 7.80 (dd, 1H), 7.94(d, 1H) Ia.227 3-Cl, C₂H₅ tetrahydro-2H- 1.20-1.40(m, 3H), 4-i-C₃H₇ pyran-4-yl 1.28(d, 6H), 1.80-2.05(m, 4H), 3.35-3.55(m, 5H), 3.70-4.50(m, 3H), 7.43(d, 1H), 7.81 (dd, 1H), 7.96(d, 1H) Ia.228 3-Cl, n-C₃H₇ tetrahydro-2H- 0.80-1.00(m, 3H), 4-i-C₃H₇ pyran-4-yl 1.28(d, 6H), 1.60-2.10(m, 6H), 3.28-3.53(m, 4H), 3.45(sept., 1H), 3.70-4.45 (m, 3H), 7.43(d, 1H), 7.81(dd, 1H), 7.95 (d, 1H) Ia.229 3-Cl, i-C₃H₇ tetrahydro-2H- 1.28(d, 6H), 4-i-C₃H₇ pyran-4-yl 1.45(s, 6H), 1.65-2.30(m, 4H), 3.34-3.40(m, 2H), 3.43(sept., 1H), 3.40-3.68(m, 1H), 3.75-3.90 (m, 1H), 4.00-4.13 (m, 2H), 7.43(d, 1H), 7.80(dd, 1H), 7.94 (d, 1H) Ia.388 2-CF₃ CH₃ tetrahydro-2H- 1.75-2.00(m, 4H), pyran-4-yl 2.95-3.10(m, 3H), 3.25-3.60(m, 2H), 3.60-3.80 and 4.40-4.55(2m, together 1H), 3.97-4.15(m, 2H), 7.57(d, 1H), 7.72 (t, 1H), 7.79(t, 1H), 7.89(d, 1H) Ia.389 2-CF₃ C₂H₅ tetrahydro-2H- 1.20-1.45(m, 3H), pyran-4-yl 1.80-2.05(m, 4H), 3.30-3.55(m, 4H), 3.40-4.50(m, 3H), 7.57(d, 1H), 7.72(t, 1H), 7.80 (t, 1H), 7.89(d, 1H) Ia.391 2-CF₃ i-C₃H₇ tetrahydro-2H- 1.47(d, 6H), pyran-4-yl 1.70-2.40(m, 4H), 3.38(t, 2H), 3.47-3.66(m, 1H), 3.70-3.90(m, 1H), 3.98-4.11(m, 2H), 7.57(d, 1H), 7.73 (t, 1H), 7.80(t, 1H), 7.89(d, 1H) Ib.3 H n-C₃H₇ tetrahydrofuran- 0.85-1.00(m, 3H), 3-yl 1.65-1.90(m, 2H), 2.05-2.20(m, 1H), 2.30-2.46(m, 1H), 3.30-3.51(m, 2H), 3.60-4.18(m, 4H), 4.45-4.70(m, 1H), 7.41(t, 1H), 7.52 (t, 2H), 7.91(d, 2H) Ib.12 2-F n-C₃H₇ tetrahydrofuran- 0.80-1.05(m, 3H), 3-yl 1.50-1.90(m, 2H), 2.05-2.20(m, 1H), 2.34-2.43(m, 1H), 3.32-3.50(m, 2H), 3.60-4.15(m, 4H), 4.45-4.75(m, 1H), 7.27-7.36(m, 2H), 7.49-7.59(m, 2H) Ib.21 2-Cl n-C₃H₇ tetrahydrofuran- 0.80-1.02(m, 3H), 3-yl 1.60-1.90(m, 2H), 2.05-2.20(m, 1H), 2.35-2.45(m, 1H), 3.34-3.50(m, 2H), 3.65-4.17(m, 4H), 4.45-4.90(m, 1H), 7.44-7.55(m, 3H), 7.61(d, 1H) Ib.30 2-Br n-C₃H₇ tetrahydrofuran- 0.80-1.02(m, 3H), 3-yl 1.60-1.90(m, 2H), 2.00-2.25(m, 1H), 2.32-2.48(m, 1H), 3.31-3.52(m, 2H), 3.60-4.20(m, 4H), 4.40-4.80(m, 1H), 7.40-7.57(m, 3H), 7.79(d, 1H) Ie.2 H C₂H₅ tetrahydro-2H- 1.13-1.40(m, 3H), thiopyran-4-yl 1.85-2.35(m, 4H), 2.60-2.95(m, 4H), 3.35-3.65 and 3.95-4.20(2m, together 3H), 7.92 (d, 2H) Ie.3 H n-C₃H₇ tetrahydro-2H- 0.80-1.05(m, 3H), thiopyran-4-yl 1.55-1.85(m, 2H), 1.88-2.17(m, 2H), 2.19-2.35(m, 2H), 2.60-2.95(m, 4H), 3.25-3.45(m, 2H), 3.47-3.64 and 3.97-4.16(2m, together 3H), 7.41 (t, 1H), 7.52(t, 2H), 7.91(d, 2H) Ie.10 2-F CH₃ tetrahydro-2H- 1.85-2.05(m, 2H), thiopyran-4-yl 2.15-2.30(m, 2H), 2.65-2.97(m, 4H), 3.06(s, 3H), 3.40-3.60 and 4.15-4.30(2m, together 1H), 7.22-7.40(m, 2H), 7.47-7.60(m, 2H) Ie.12 2-F n-C₃H₇ tetrahydro-2H- 0.80-1.03(m, 3H), thiopyran-4-yl 1.54-1.83(m, 2H), 1.90-2.17(m, 2H), 2.18-2.40(m, 2H), 2.65-2.95(m, 4H), 3.30-3.44(m, 2H), 3.45-3.64 and 3.97-4.18(2m, together 3H), 7.25-7.39(m, 2H), 7.48-7.61(m, 2H) Ie.19 2-Cl CH₃ tetrahydro-2H- 1.85-2.10(m, 2H), thiopyran-4-yl 2.15-2.30(m, 2H), 2.65-2.95(m, 4H), 3.05(m, 3H), 3.40-3.60 and 4.15-4.30(2m, together 1H), 7.40-7.65(m, 4H) Ie.20 2-Cl C₂H₅ tetrahydro-2H- 1.15-1.40(m, 3H), thiopyran-4-yl 1.85-2.35(m, 4H), 2.60-2.95(m, 4H), 3.40-3.62 and 4.02-4.22(2m, together 3H), 7.40-7.65(m, 4H) Ie.21 2-Cl n-C₃H₇ tetrahydro-2H- 0.80-1.03(m, 3H), thiopyran-4-yl 1.55-1.82(m, 2H), 1.88-2.15(m, 2H), 2.20-2.35(m, 2H), 2.65-2.92(m, 4H), 3.30-3.43(m, 2H), 3.45-3.63 and 4.00-4.20(2m, together 3H), 7.43-7.63(m, 4H), Ie.28 2-Br CH₃ tetrahydro-2H- 1.90-2.10(m, 2H), thiopyran-4-yl 2.15-2.30(m, 2H), 2.65-2.95(m, 4H), 3.05(m, 3H), 3.40-3.60 and 4.15-4.30(2m, together 1H), 7.40-7.55(m, 3H), 7.79(d, 1H) Ie.29 2-Br C₂H₅ tetrahydro-2H- 1.15-1.40(m, 3H), thiopyran-4-yl 1.85-2.35(m, 4H), 2.60-2.95(m, 4H), 3.40-3.62 and 4.00-4.20(2m, together 3H), 7.35-7.55(m, 3H), 7.77(d, 1H) Ie.30 2-Br n-C₃H₇ tetrahydro-2H- 0.80-1.02(m, 3H), thiopyran-4-yl 1.55-1.82(m, 2H), 1.88-2.15(m, 2H), 2.17-2.35(m, 2H), 2.60-2.95(m, 4H), 3.30-3.43(m, 2H), 3.45-3.63 and 4.05-4.20(2m, together 3H), 7.40-7.55(m, 3H), 7.79(d, 1H) Ie.38 2-CH₃ C₂H₅ tetrahydro-2H- 1.15-1.40(m, 3H), thiopyran-4-yl 1.90-2.35(m, 4H), 2.30(s, 3H), 2.60-2.95(m, 4H), 3.43-3.60 and 4.00-4.20(2m, together 3H), 7.30-7.47(m, 3H) Ie.155 2,6-Cl₂ C₂H₅ tetrahydro-2H- 1.15-1.40(m, 3H), thiopyran-4-yl 1.90-2.35(m, 4H), 2.55-2.95(m, 4H), 3.40-3.60 and 4.05-4.25(2m, together 3H), 7.43-7.58(m, 3H) Ie.156 2,6-Cl₂ n-C₃H₇ tetrahydro-2H- 0.80-1.05(m, 3H), thiopyran-4-yl 1.50-1.84(m, 2H), 1.87-2.14(m, 2H), 2.17-2.30(m, 2H), 2.60-2.95(m, 4H), 3.25-3.55 and 4.05-4.20(2m, together 3H), 7.42-7.58(m, 3H) Ie.199 2-Cl, CH₃ tetrahydro-2H- 1.90-2.05(m, 2H), 6-CH₃ thiopyran-4-yl 2.15-2.30(m, 2H), 2.27(s, 3H), 2.65-2.95(m, 4H), 3.04(m, 3H), 3.40-3.60 and 4.15-4.30(2m, together 1H), 7.22-7.45(m, 3H) Ie.200 2-Cl, C₂H₅ tetrahydro-2H- 1.15-1.40(m, 3H), 6-CH₃ thiopyran-4-yl 1.85-2.40(m, 4H), 2.29(s, 3H), 2.55-2.95(m, 4H), 3.40-3.65 and 4.05-4.25(2m together 3H), 7.25-7.47(m, 3H) Ie.201 2-Cl, n-C₃H₇ tetrahydro-2H- 0.80-1.05(m, 3H), 6-CH₃ thiopyran-4-yl 1.55-1.85(m, 2H), 1.90-2.15(m, 2H), 2.17-2.40(m, 2H), 2.29(s, 3H), 2.60-2.95(m, 4H), 3.25-3.60 and 4.05-4.20(2m, together 3H), 7.25-7.45(m, 3H) Ie.226 3-Cl, CH₃ tetrahydro-2H- 1.28(d, 6H), 4-i-C₃H₇ thiopyran-4-yl 1.90-2.05(m, 2H), 2.15-2.30(m, 2H), 2.65-2.95(m, 4H), 3.04(m, 3H), 3.44(sept., 1H), 3.50-3.60 and 4.15-4.30(2m, together 1H), 7.43 (d, 1H), 7.79 (dd, 1H), 7.93(d, 1H) Ie.227 3-Cl, C₂H₅ tetrahydro-2H- 1.15-1.40(m, 3H), 4-i-C₃H₇ thiopyran-4-yl 1.28(d, 6H), 1.90-2.25(m, 4H), 2.62-2.95(m, 4H), 3.35-3.60 and 4.00-4.20(2m, together 3H), 3.45 (sept., 1H), 7.43 (d, 1H), 7.80(dd, 1H), 7.94(d, 1H) Ie.228 3-Cl, n-C₃H₇ tetrahydro-2H- 0.80-1.05(m, 3H), 4-i-C₃H₇ thiopyran-4-yl 1.28(d, 6H), 1.55-1.80(m, 2H), 1.90-2.15(m, 2H), 2.20-2.35(m, 2H), 2.65-2.90(m, 4H), 3.30-3.60 and 3.95-4.15(2m, together 3H), 3.44 (sept., 1H), 7.43 (d, 1H), 7.81(dd, 1H), 7.96(d, 1H) Ie.388 2-CF₃ CH₃ tetrahydro-2H- 1.75-2.12(m, 2H), thiopyran-4-yl 2.15-2.30(m, 2H), 2.60-2.98(m, 4H), 3.01 and 3.09(2s, together 3H), 3.35-3.60 and 4.15-4.30(2m, together 1H), 7.50-7.95(m, 4H) Ie.389 2-CF₃ C₂H₅ tetrahydro-2H- 1.10-1.40(m, 3H), thiopyran-4-yl 1.80-2.35(m, 4H), 2.55-2.95(m, 4H), 3.30-3.60 and 4.00-4.20(2m, together 3H), 7.58 (d, 1H), 7.72(t, 1H), 7.80(t, 1H), 7.90 (d, 1H) If.228 3-Cl, n-C₃H₇ tetrahydrothio- 0.85-1.00(m, 3H), 4-i-C₃H₇ phen-3-yl 1.28(d, 6H), 1.65-1.80(m, 2H), 2.00-2.45(m, 2H), 2.80-3.10(m, 4H), 3.25-3.45(m, 2H), 3.44(sept., 1H), 4.25-4.50(m, 1H), 7.43(d, 1H), 7.79 (dd, 1H), 7.93(d, 1H) Ih.3 H n-C₃H₇ 2,4-dimethyl- 0.98(t, 3H), thiophen-3-yl 1.60-1.90(m, 2H), 2.17(s, 3H), 2.35 (s, 3H), 3.53(ddd, 1H), 3.81(ddd, 1H), 6.69(s, 1H), 7.35 (t, 1H), 7.46(t, 2H), 7.78(d, 2H) Ih.12 2-F n-C₃H₇ 2,4-dimethyl- 0.98(t, 3H), thiophen-3-yl 1.60-1.90(m, 2H), 2.17(s, 3H), 2.34 (s, 3H), 3.52(ddd, 1H), 3.82(ddd, 1H), 6.70(s, 1H), 7.17-7.30(m, 2H), 7.35-7.50(m, 2H) Ih.21 2-Cl n-C₃H₇ 2,4-dimethyl- 0.99(t, 3H), thiophen-3-yl 1.60-1.90(m, 2H), 2.17(s, 3H), 2.34 (s, 3H), 3.52 (ddd, 1H), 3.83 (ddd, 1H), 6.69 (s, 1H), 7.34-7.52 (m, 4H) Ih.30 2-Br n-C₃H₇ 2,4-dimethyl- 0.98(t, 3H), thiophen-3-yl 1.60-1.90(m, 2H), 2.18(s, 3H), 2.35 (s, 3H), 3.52 (ddd, 1H), 3.84 (ddd, 1H), 6.70 (s, 1H) 7.30-7.47 (m, 3H), 7.67(d, 1H) Ih.39 2-CH₃ n-C₃H₇ 2,4-dimethyl- 0.98(t, 3H), thiophen-3-yl 1.60-1.90(m, 2H), 2.01(s, 3H), 2.17 (s, 3H), 2.35(s, 3H), 3.54(ddd, 1H), 3.82 (ddd, 1H), 6.69 (s, 1H), 7.15-7.40 (m, 4H) Ih.156 2,6-Cl₂ n-C₃H₇ 2,4-dimethyl- 0.98(t, 3H), thiophen-3-yl 1.60-1.90(m, 2H), 2.18(s, 3H), 2.34 (s, 3H), 3.51 (ddd, 1H), 3.85 (ddd, 1H), 6.67 (s, 1H), 7.35-7.45 (m, 3H) Ih.201 2-Cl, n-C₃H₇ 2,4-dimethyl- 0.98(t, 3H), 6-CH₃ thiophen-3-yl 1.60-1.90(m, 2H), 2.08(s, 3H), 2.18 (s, 3H), 2.35(s, 3H), 3.52(ddd, 1H), 3.83 (ddd, 1H), 6.68 (s, 1H), 7.12-7.35 (m, 3H) Ih.228 3-Cl, n-C₃H₇ 2,4-dimethyl- 0.98(t, 3H), 1.24 4-i-C₃H₇ thiophen-3-yl (d, 6H), 1.60-1.87 (m, 2H), 2.16(s, 3H), 2.34(s, 3H), 3.40 (sept., 1H), 3.53 (ddd, 1H), 3.81(ddd, 1H), 6.69(s, 1H), 7.37(d, 1H), 7.68 (dd, 1H), 7.80(d, 1H) Ih.390 2-CF₃ n-C₃H₇ 2,4-dimethyl- 0.98(t, 3H), thiophen-3-yl 1.60-1.90(m, 2H), 2.15(s, 3H), 2.33 (s, 3H), 3.52 (ddd, 1H), 3.82 (ddd, 1H), 6.70 (s, 1H), 7.39(d, 1H), 7.64(t, 1H), 7.70 (t, 1H), 7.80(d, 1H)

TABLE 5 I

¹H NMR [ppm]/ No. R¹ R² Het MS [m/z] Ii.47 CH₂—CH₂—Cl C₂H₅ tetrahydro-2H- 1.13-1.37(m, 3H), pyran-4-yl 1.80-2.05(m, 4H), 3.30-3.55(m, 4H), 3.64-3.80 and 3.97-4.12(2m, together 3H), 3.90 (t, 2H), 4.32(t, 2H) Ii.48 CH₂—CH₂—Cl n-C₃H₇ tetrahydro-2H- 0.75-1.00(m, 3H), pyran-4-yl 1.50-2.03(m, 6H), 3.22-3.50(m, 4H), 3.62-3.80 and 3.97-4.12(2m, together 3H), 3.90 (t, 2H), 4.32(t, 2H) Ii.49 CH₂—CH₂—Cl i-C₃H₇ tetrahydro-2H- 1.44(s, 6H), pyran-4-yl 1.64-2.40(m, 4H), 3.37(t, 2H), 3.45-3.60(m, 1H), 3.70-3.85(m, 1H), 3.90(t, 2H), 4.00-4.12(m, 2H), 4.32(t, 2H) In.47 CH₂—CH₂—Cl C₂H₅ tetrahydro-2H- 1.12-1.36(m, 3H), thiopyran-4-yl 1.90-2.12(m, 2H), 2.15-2.27(m, 2H), 2.60-2.90(m, 4H), 3.37-3.55 and 4.00-4.15(2m, together 3H), 3.90 (t, 2H), 4.32(t, 2H) In.48 CH₂—CH₂—Cl n-C₃H₇ tetrahydro-2H- 0.80-1.00(m, 3H), thiopyran-4-yl 1.55-1.80(m, 2H), 1.87-2.10(m, 2H), 2.15-2.26(m, 2H), 2.65-2.90(m, 4H), 3.20-3.60 and 3.97-4.15(2m, together 3H), 3.90 (t, 2H), 4.32(t, 2H) Iq. 48 CH₂—CH₂—Cl n-C₃H₇ 2,4-dimethyl- 343 [M]* thiophen-3-yl

USE EXAMPLES

The herbicidal action of the substituted tetrazolinonecarboxamides of the formula I was demonstrated by greenhouse experiments:

The culture containers used were plastic pots containing loamy sand with approximately 3.0% of humus as substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with translucent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active ingredients.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The application rate for the post-emergence treatment was 1.0 kg of a.s. (active substance)/ha.

Depending on the species, the plants were kept at 10 to 25° C. or 20 to 35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage, or normal course of growth. Using the compound Ia. 20, for example, damage of 80 to 85% was achieved by the post-emergence method in the plant species listed below:

Scientific Name Common Name Alopecurus myosuroides blackgrass Echinochloa crus-galli barnyardgrass 

We claim:
 1. A substituted tetrazolinonecarboxamide of the formula I

where the variables have the following meaning: Het is furan-3-yl or thiophen-3-yl, where the abovementioned heterocycles may carry one or two substituents selected from a group consisting of halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; R¹ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₄-haloalkylsulfonyl-C₁-C₄-alkyl, C₂-C₆-alkenyl, cyano-C₃-C₆-alkenyl, C₂-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₅-C₈-cycloalkenyl, C₅-C₈-cycloalkenyl-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, 3- to 7-membered heterocyclyl, which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C₁-C₄-alkyl, which may contain a carbonyl or thiocarbonyl ring member, where the cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings may in each case be unsubstituted or carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkylcarbonyloxy and C₁-C₄-haloalkylcarbonyloxy, and where the heterocyclyl rings are in each case saturated, partially saturated or completely unsaturated and aromatic and contain one to three heteroatoms selected from a group consisting of one to three nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms, R² is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, 3- to 7-membered heterocyclyl, which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C₁-C₄-alkyl, which may contain a carbonyl or thiocarbonyl ring member, where the cycloalkyl rings, phenyl rings or heterocyclyl rings are in each case unsubstituted or carry one to four substituents, in each case selected from the group consisting of halogen , cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄ -alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkylcarbonyloxy and C₁-C₄-haloalkylcarbonyloxy, and where the heterocyclyl rings are in each case saturated, partially saturated or completely unsaturated and aromatic and contain one to three heteroatoms selected from a group consisting of one to three nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms.
 2. A process for preparing substituted tetrazolinonecarboxamides of the formula I as claimed in claim 1, which comprises reacting a tetrazolinone of the formula II

in the presence of a base with a carbamoyl chloride of the formula III

or initially deprotonating a tetrazolinone of the formula II with a base and subsequently reacting it with a carbamoyl chloride of the formula III.
 3. A process for preparing substituted tetrazolinonecarboxamides of the formula I as claimed in claim 1, which comprises reacting a tetrazolinonecarbonyl chloride of the formula VI

in the presence of a base with an amine of the formula V R²—NH—Het  V.
 4. A carbamoyl chloride of the formula III

wherein Het is furan-3-yl or thiophen-3-yl, where the abovementioned heterocycles may carry one or two substituents selected from a group consisting of halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl; R² is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, 3- to 7-membered heterocyclyl, which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C₁-C₄-alkyl, which may contain a carbonyl or thiocarbonyl ring member, where the cycloalkyl rings, phenyl rings or heterocyclyl rings are in each case unsubstituted or carry one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alklcarbonyloxy and C₁-C₄-haloalkylcarbonyloxy, and where the heterocyclyl rings are in each case saturated, partically saturated or completely unsaturated and aromatic and contain one to three heteroatoms selected from a group consisting of one to three nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms.
 5. A process for preparing the carbamoyl chloride of formula III defined in claim 4, which comprises reacting an amine of formula V R²—NH—Het  (V) or an acid addition salt of the amine with a phosgenating agent selected from the group of phosqene, disphosgene and triphosgene.
 6. A herbicidal composition which comprises a herbicidally effective amount of at least one substituted triazolinonecarboxamide of the formula I as claimed in claim 1, and at least one customary additive.
 7. A process for preparing herbicidally active compositions, which comprises mixing a herbicidally effective amount of at least one substituted tetrazolinone carboxamide of the formula I as claimed in claim 1 with at least one customary additive.
 8. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one substituted tetrazolinone carboxamide of the formula I as claimed in claim 1 to act on plants, their habitat or on seed.
 9. The tetrazolinonecarboxamide of formula I defined in claim 1, wherein R¹ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl-C₁ 14 C₄-alkyl, C₁-C₄-haloalkylsulfonyl-C₁-C₄-alkyl, C₃-C₆-alkenyl, cyano-C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₅-C₈-cycloalkenyl, C₅-C₈-cycloalkenyl-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, 3- to 7-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7- membered heterocyclyl-C₁-C₄-alkyl which may contain a carbonyl or thiocarbonyl ring member, where the cycloalkyl rings, cycloalkenyl rings, phenyl rings and heterocyclyl rings are in each case unsubstituted or carry one to four substituents selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkylcarbonyloxy and C₁-C₄-haloalkylcarbonyloxy.
 10. The tetrazolinonecarboxamide of formula I defined in claim 1, wherein R¹ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₄-alkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₅-C₈-cycloalkenyl, C₅-C₈-cycloalkenyl-C₁-C₄-alkyl, phenyl, phenyl-C₁-C₄-alkyl, 3- to 7-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member, or 3- to 7-membered heterocyclyl-C₁-C₄-alkyl which may contain a carbonyl or thiocarbonyl ring member, where the cycloalkyl rings, cycloalkenyl rings, phenyl rings and heterocyclyl rings are in each case unsubstituted or carry one to four substituents selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl and C₁-C₄-alkylcarbonyl.
 11. The tetrazolinonecarboxamide of formula I defined in claim 1, wherein R¹ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, phenyl, phenyl-C₁-C₄-alkyl or 3- to 7-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member, where the cycloalkyl rings, cycloalkenyl rings, phenyl rings and heterocyclyl rings are in each case unsubstituted or carry one to four substituents selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl and C₁-C₄-alkylcarbonyl.
 12. The tetrazolinonecarboxamide of formula I defined in claim 1, wherein R¹ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, phenyl or C₃-C₇-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member, where the cycloalkyl rings, cycloalkenyl rings, phenyl rings and heterocyclyl rings are in each case be unsubstituted or carry one to four substituents selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl and C₁-C₄-alkylcarbonyl.
 13. The tetrazolinonecarboxamide of formula I defined in claim 1, wherein R¹ is phenyl which is unsubstituted or carries one to four substituents selected from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-halo-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl and C₁-C₄-alkylcarbonyl.
 14. The tetrazolinonecarboxamide of formula I defined in claim 1, wherein R² is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, phenyl or benzyl.
 15. The tetrazolinonecarboxamide of formula I defined in claim 1, wherein R² is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, phenyl or benzyl. 